Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 12
Submit an article Journal homepage
591
Views
64
CrossRef citations to date
0
Altmetric
Original Articles

An Efficient Deprotective Method for Allylic Alcohols Protected as Methoxyethoxymethyl (MEM) And Methoxymethyl (MOM) Ethers

H. Monti Laboratoire Associé au C.N.R.S. n° 109, Université d'Aix-Marseille III, Rue Henri Poincaré, 13397, Marseille Cedex 13, France
,
G. Léandri Laboratoire Associé au C.N.R.S. n° 109, Université d'Aix-Marseille III, Rue Henri Poincaré, 13397, Marseille Cedex 13, France
,
M. Klos-ringuet Laboratoire Associé au C.N.R.S. n° 109, Université d'Aix-Marseille III, Rue Henri Poincaré, 13397, Marseille Cedex 13, France
&
C. Corriol Laboratoire Associé au C.N.R.S. n° 109, Université d'Aix-Marseille III, Rue Henri Poincaré, 13397, Marseille Cedex 13, France
Pages 1021-1026 | Published online: 06 Feb 2007

Citations (64)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (2)

Yungui Peng, Changyun Ji, Yingchun Chen, Chengzhi Huang & Yaozhong Jiang. (2004) An Efficient and Selective Deprotecting Method for Methoxymethyl Ethers. Synthetic Communications 34:23, pages 4325-4330.
Read now
Satoshi YAMAUCHI & Yoshiro KINOSHITA. (2000) Stereoselective Model Synthesis of the Optically Active Olivil Type of Lignan from D-Xylose. Bioscience, Biotechnology, and Biochemistry 64:8, pages 1563-1571.
Read now

Articles from other publishers (62)

Marko Nesic, Maegen M. Kincanon, David B. Ryffel & David Sarlah. (2020) A new approach towards the synthesis of bielschowskysin: Synthesis and photochemistry of an advanced macrocyclic enedione intermediate. Tetrahedron 76:51, pages 131318.
Crossref
Ranjan Kumar Acharyya, Rohan Kalyan Rej & Samik Nanda. (2018) Exploration of Ring Rearrangement Metathesis Reaction: A General and Flexible Approach for the Rapid Construction [5, n ]-Fused Bicyclic Systems en Route to Linear Triquinanes . The Journal of Organic Chemistry 83:4, pages 2087-2103.
Crossref
Eun-Kyung Jung, Nora Dittrich, Lisa I. Pilkington, Claire E. Rye, Euphemia Leung & David Barker. (2015) Synthesis of aza-derivatives of tetrahydrofuran lignan natural products. Tetrahedron 71:50, pages 9439-9456.
Crossref
José Manuel Botubol, María Jesús Durán-Peña, Antonio J. Macías-Sánchez, James R Hanson, Isidro G. Collado & Rosario Hernández-Galán. (2014) The Asymmetric Total Synthesis of Cinbotolide: A Revision of the Original Structure. The Journal of Organic Chemistry 79:23, pages 11349-11358.
Crossref
Christian Chapuis, David Skuy, Jean‐Yves de Saint Laumer & Robert Brauchli. (2014) endo / exo Stereoselectivity in Diels  Alder Reactions of α , β ‐Dialkylated Conjugated Enals to Cyclic 1,3‐Dienes: Intermediates in the Synthesis of (−)‐ β ‐Santalol and Its Analogs . Chemistry & Biodiversity 11:10, pages 1470-1516.
Crossref
. 2014. Greene's Protective Groups in Organic Synthesis. Greene's Protective Groups in Organic Synthesis 17 471 .
Fu-Min Zhang & Yong-Qiang Tu. (2014) Towards the real didemnaketal A: total syntheses of two C-21 stereoisomers of the proposed didemnaketal A. Tetrahedron Letters 55:28, pages 3784-3787.
Crossref
Shouliang Yang, Yumeng Xi, Jia-Hua Chen & Zhen Yang. (2014) Asymmetric total synthesis of (−)-cebulactam A1. Organic Chemistry Frontiers 1:1, pages 91.
Crossref
Nina Duhamel, Claire E. Rye & David Barker. (2013) Total Synthesis of ent ‐Hyperione A and ent ‐Hyperione B . Asian Journal of Organic Chemistry 2:6, pages 491-493.
Crossref
Laëtitia Chausset-Boissarie, Roman Àrvai, Graham R. Cumming, Laure Guénée & E. Peter Kündig. (2012) Asymmetric synthesis of (+)-vertine and (+)-lythrine. Organic & Biomolecular Chemistry 10:32, pages 6473.
Crossref
Jack Li-Yang Chen & Margaret A. Brimble. (2011) Synthesis of the Bis-Spiroacetal Core of the Antimitotic Agent Spirastrellolide B. The Journal of Organic Chemistry 76:22, pages 9417-9428.
Crossref
Hiromichi Fujioka, Yutaka Minamitsuji, Ozora Kubo, Kento Senami & Tomohiro Maegawa. (2011) The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups. Tetrahedron 67:16, pages 2949-2960.
Crossref
Jae Hyun Han, Young Eun Kwon, Jeong-Hun Sohn & Do Hyun Ryu. (2010) A facile method for the rapid and selective deprotection of methoxymethyl (MOM) ethers. Tetrahedron 66:9, pages 1673-1677.
Crossref
Laetitia Chausset-Boissarie, Roman Àrvai, Graham R. Cumming, Céline Besnard & E. Peter Kündig. (2010) Total synthesis of (±)-Vertine with Z-selective RCM as a key step. Chemical Communications 46:34, pages 6264.
Crossref
Jack Li-Yang Chen & Margaret A. Brimble. (2010) Synthesis of the bis-spiroacetal C25–C40 moiety of the antimitotic agent spirastrellolide B using a bis-dithiane deprotection/spiroacetalisation sequence. Chemical Communications 46:22, pages 3967.
Crossref
J.S. Yadav, B. Ganganna, Dinesh C. Bhunia & P. Srihari. (2009) NbCl5 mediated deprotection of methoxy methyl ether. Tetrahedron Letters 50:30, pages 4318-4320.
Crossref
Yingpeng Su, Yanfen Xu, Junjie Han, Jiyue Zheng, Jing Qi, Tuo Jiang, Xinfu Pan & Xuegong She. (2009) Total Synthesis of (−)-Bitungolide F. The Journal of Organic Chemistry 74:7, pages 2743-2749.
Crossref
Hiromichi Fujioka, Ozora Kubo, Kento Senami, Yutaka Minamitsuji & Tomohiro Maegawa. (2009) Remarkable effect of 2,2′-bipyridyl: mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)–2,2′-bipyridyl. Chemical Communications:29, pages 4429.
Crossref
Fumihiro Ito, Takuya Kumamoto, Kentaro Yamaguchi & Tsutomu Ishikawa. (2009) Synthetic studies toward miroestrols: trials for elongation of the methyl group of 5-substituted 2-methyl-2-cyclohexanone to 3-methyl-2-butenyl function. Tetrahedron 65:4, pages 771-785.
Crossref
Matthew J. Fleming, Helen A. McManus, Alena Rudolph, Walter H. Chan, Jérémy Ruiz, Chris Dockendorff & Mark Lautens. (2008) Concise Enantioselective Total Syntheses of (+)‐Homochelidonine, (+)‐Chelamidine, (+)‐Chelidonine, (+)‐Chelamine and (+)‐Norchelidonine by a Pd II ‐Catalyzed Ring‐Opening Strategy . Chemistry – A European Journal 14:7, pages 2112-2124.
Crossref
Yasuhito Koyama, Ryo Yamaguchi & Keisuke Suzuki. (2008) Total Synthesis and Structure Assignment of the Anthrone C‐Glycoside Cassialoin. Angewandte Chemie International Edition 47:6, pages 1084-1087.
Crossref
Yasuhito Koyama, Ryo Yamaguchi & Keisuke Suzuki. (2008) Total Synthesis and Structure Assignment of the Anthrone C‐Glycoside Cassialoin. Angewandte Chemie 120:6, pages 1100-1103.
Crossref
Helen A. McManus, Matthew J. Fleming & Mark Lautens. (2006) Enantioselective Total Synthesis of (+)‐Homochelidonine by a Pd II ‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso ‐Azabicyclic Alkene with an Aryl Boronic Acid . Angewandte Chemie International Edition 46:3, pages 433-436.
Crossref
Helen A. McManus, Matthew J. Fleming & Mark Lautens. (2006) Enantioselective Total Synthesis of (+)‐Homochelidonine by a Pd II ‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso ‐Azabicyclic Alkene with an Aryl Boronic Acid . Angewandte Chemie 119:3, pages 437-440.
Crossref
H. Marlon Zhong, Jeong-Hun Sohn & Viresh H. Rawal. (2006) Studies toward the Asymmetric Synthesis of the Right Part of the Mycalamides. The Journal of Organic Chemistry 72:2, pages 386-397.
Crossref
Qinggang Huang, Qiaoling Wang, Jiyue Zheng, Jiyong Zhang, Xinfu Pan & Xuegong She. (2007) A general route to 5,6-seco-hexahydrodibenzopyrans and analogues: first total synthesis of (+)-Machaeridiol B and (+)-Machaeriol B. Tetrahedron 63:4, pages 1014-1021.
Crossref
M. Aquino, I. Bruno, R. Riccio & L. Gomez-Paloma. (2006) Regioselective Entry to Bromo-γ-hydroxybutenolides:  Useful Building Blocks for Assemblying Natural Product-Like Libraries. Organic Letters 8:21, pages 4831-4834.
Crossref
Valquiria Aragao, Mauricio Constantino, Adilson Beatriz & Gil José da Silva. (2005) Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester. Molecules 10:11, pages 1413-1418.
Crossref
G.V.M. Sharma, K. Laxma Reddy, P. Sree Lakshmi & Palakodety Radha Krishna. (2004) An efficient protocol for the preparation of MOM ethers and their deprotection using zirconium(IV) chloride. Tetrahedron Letters 45:50, pages 9229-9232.
Crossref
Martin G Banwell, Alison J Edwards, Gwion J Harfoot & Katrina A Jolliffe. (2004) A chemoenzymatic synthesis of the linear triquinane (?)-hirsutene and identification of possible precursors to the naturally occurring (+)-enantiomer. Tetrahedron 60:3, pages 535-547.
Crossref
S Venkat Reddy, R Jagadeeshwar Rao, U Sampath Kumar & J Madhusudana Rao. (2003) Highly Efficient and Convenient Deprotection of Methoxymethyl Ethers and Esters Using Bismuth Triflate in an Aqueous Medium. Chemistry Letters 32:11, pages 1038-1039.
Crossref
C. Ramesh, N. Ravindranath & Biswanath Das. (2003) Simple, Efficient, and Selective Deprotection of Phenolic Methoxymethyl Ethers Using Silica-Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst 1 . The Journal of Organic Chemistry 68:18, pages 7101-7103.
Crossref
Thorsten Blume, Marc Guttzeit, Joachim Kuhnke & Ludwig Zorn. (2003) Two Syntheses of FF-MAS. Organic Letters 5:11, pages 1837-1839.
Crossref
Mukund K. Gurjar, Ravi Nagaprasad & C.V. Ramana. (2003) Total synthesis of microcarpalide. Tetrahedron Letters 44:14, pages 2873-2875.
Crossref
Yong-Gang Wang & Yuichi Kobayashi. (2002) Formal Total Synthesis of Fostriecin. Organic Letters 4:26, pages 4615-4618.
Crossref
Anthony D. William & Yuichi Kobayashi. (2002) Synthesis of Tetrahydrocannabinols Based on an Indirect 1,4-Addition Strategy. The Journal of Organic Chemistry 67:25, pages 8771-8782.
Crossref
Martin G. Banwell, Alison J. Edwards, Gwion J. Harfoot & Katrina A. Jolliffe. (2002) A chemoenzymatic synthesis of (−)-hirsutene from toluene. J. Chem. Soc., Perkin Trans. 1:22, pages 2439-2441.
Crossref
Gianpietro Borsotti, Gianfranco Guglielmetti, Silvia Spera & Ezio Battistel. (2001) Synthesis of phosphatidylcholines containing ricinoleic acid. Tetrahedron 57:51, pages 10219-10227.
Crossref
Adam A. Galan. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Peter G. M. Wuts. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Peter G. M. Wuts. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Adam Shih-Yuan Lee, Yi-Jung Hu & Shu-Fang Chu. (2001) A simple and highly efficient deprotecting method for methoxymethyl and methoxyethoxymethyl ethers and methoxyethoxymethyl esters. Tetrahedron 57:11, pages 2121-2126.
Crossref
Fumito Tani, Mikiya Matsu-ura, Shinya Nakayama, Mari Ichimura, Nobuhumi Nakamura & Yoshinori Naruta. (2001) Synthesis and Characterization of Alkanethiolate-Coordinated Iron Porphyrins and Their Dioxygen Adducts as Models for the Active Center of Cytochrome P450:  Direct Evidence for Hydrogen Bonding to Bound Dioxygen. Journal of the American Chemical Society 123:6, pages 1133-1142.
Crossref
Arun K. Ghosh & Yong Wang. (2000) Total Synthesis of (−)-Laulimalide. Journal of the American Chemical Society 122:44, pages 11027-11028.
Crossref
Fumihiko Yoshimura, Shinji Kawata & Masahiro Hirama. (1999) Synthetic study of kedarcidin chromophore: atropselective construction of the ansamacrolide. Tetrahedron Letters 40:47, pages 8281-8285.
Crossref
Sandrine Piguel, Gerardo Ulibarri & David S. Grierson. (1999) Studies toward the construction of the allyltrisulfide component in esperamicin-A1 from 5-ketoshikimic acid derivatives: Part 2. Tetrahedron Letters 40:2, pages 295-298.
Crossref
Satoru Kaneko, Noriyuki Nakajima, Mayumi Shikano, Tadashi Katoh & Shiro Terashima. (1998) Synthetic studies of huperzine A and its fluorinated analogues. 2. Synthesis and acetylcholinesterase inhibitory activity of novel fluorinated huperzine A analogues. Tetrahedron 54:21, pages 5485-5506.
Crossref
X. Eric Hu & Thomas P. Demuth. (1998) Synthesis of 2-(Hydroxymethyl)-1β-methylcarbapenem. Chemoselective Organometallic Addition to 3-Substituted 4-[( R )-1-Carboxyethyl]azetidin-2-one . The Journal of Organic Chemistry 63:5, pages 1719-1723.
Crossref
K. C. Nicolaou, Eddy W. Yue, Susan la Greca, Alan Nadin, Zhen Yang, James E. Leresche, Tatsuo Tsuri, Yoshimitsu Naniwa & Francesco de Riccardis. (2006) Synthesis of Zaragozic Acid A/Squalestatin S1. Chemistry – A European Journal 1:7, pages 467-494.
Crossref
Gerhard Buchbauer, Philippine Lebada, Helmut Spreitzer & Peter Wolschann. (2006) Structure‐odor relationships of sandalwood odorants: Synthesis of ( Z )‐7‐oxa‐β‐santalol . Liebigs Annalen 1995:9, pages 1693-1696.
Crossref
Wei-Shan Zhou, Wen-Ge Xie, Zhi-Hui Lu & Xin-Fu Pan. (1995) Asymmetric formal total synthesis of (–)-swainsonine. J. Chem. Soc., Perkin Trans. 1:20, pages 2599-2604.
Crossref
Edward Piers, M. Livain Breau, Yongxin Han, Guy L. Plourde & Wen-Lung Yeh. (1995) Total synthesis of cis-clerodane diterpenoids: (–)-agelasine A and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide. J. Chem. Soc., Perkin Trans. 1:8, pages 963-966.
Crossref
Carl J. Lovely & Robert W. Brueggemeier. (1994) Synthesis of 2-substituted hydroxyalkyl and aminoalkyl estradiols. Tetrahedron Letters 35:47, pages 8735-8738.
Crossref
M. A. Kishimba & B. Zwanenburg. (2010) Synthesis of carba‐strigol analogues. Recueil des Travaux Chimiques des Pays-Bas 113:1, pages 21-28.
Crossref
Marie E. Krafft, Sandra Jarrett & Olivier A. Dasse. (1993) A ligand assisted Claisen rearrangement. Tetrahedron Letters 34:51, pages 8209-8212.
Crossref
Wei-Shan Zhou & Liang-Fu Huang. (1992) Studies on steroidal plant-growth regulator 25. Concise stereoselective construction of sidechain of brassinosteroid from the intact sidechain of hyodeoxycholic acid: formal syntheses of brassinolide, 25-methylbrassinolide, 26, 27-bisnorbrassinolide and their related compounds. Tetrahedron 48:10, pages 1837-1852.
Crossref
Wei-Shan Zhou, Liang-Fu Huang, Li-Qiang Sun & Xin-Fu Pan. (1991) Studies on steroidal plant-growth regulator 21. A stereoselective construction of brassinosteroid side chain: a new practical synthesis of brassinolide and its analogues. Tetrahedron Letters 32:46, pages 6745-6748.
Crossref
Yoshitsugu Arai, Saburo Kawanami & Toru Koizumi. (1991) Novel route to some biologically important compounds starting with a common chiral, bicyclic, fused lactone: enantioselective synthesis of (–)-boschnialactone and two antithrombotics. J. Chem. Soc., Perkin Trans. 1:12, pages 2969-2975.
Crossref
Yoshitsugu Arai, Saburo Kawanami & Toru Koizumi. (1990) Enantioselective Synthesis of (−)-Boschnialactone. Chemistry Letters 19:9, pages 1585-1586.
Crossref
Jack Chiarello & Madeleine M. Joulli?. (1988) Synthetic routes to cristatic acid and derivatives. Tetrahedron 44:1, pages 41-48.
Crossref
Mauri Lounasmaa & Pekka Somersalo. (1986) Studies on the synthesis of indole alkaloids of condylocarpine type. C-4 alkylation of the 1-alkyl-3-(hydrazono)-2-piperidone system. Tetrahedron 42:5, pages 1501-1509.
Crossref
H. MONTI, G. + LEANDRI, M. KLOS‐RINGUET & C. CORRIOL. (2016) ChemInform Abstract: AN EFFICIENT DEPROTECTIVE METHOD FOR ALLYLIC ALCOHOLS PROTECTED AS METHOXYETHOXYMETHYL (MEM) AND METHOXYMETHYL (MOM) ETHERS. Chemischer Informationsdienst 15:17.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.