757
Views
50
CrossRef citations to date
0
Altmetric
Original Articles

Iodine Promoted Glycosylation with Glycosyl Iodides: α‐Glycoside Synthesis

, &
Pages 463-474 | Received 27 Jan 2005, Accepted 14 Mar 2005, Published online: 16 Aug 2006

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

Read on this site (3)

Innaiah K. Polanki, Siva H. Kurma & Asish K. Bhattacharya. (2015) Direct Glycosylation of Unprotected and Unactivated Sugars Using Bismuth Nitrate Pentahydrate . Journal of Carbohydrate Chemistry 34:4, pages 196-205.
Read now
SnehaC. Ranade & AlexeiV. Demchenko. (2013) Mechanism of Chemical Glycosylation: Focus on the Mode of Activation and Departure of Anomeric Leaving Groups. Journal of Carbohydrate Chemistry 32:1, pages 1-43.
Read now
HassanB. Lazrek, Driss Ouzebla & Abdesslem Faraj. (2011) AN ECONOMICAL SYNTHESIS OF D- AND L-PYRIMIDINE ARABINO- AND RIBONUCLEOSIDES. Nucleosides, Nucleotides & Nucleic Acids 30:3, pages 227-234.
Read now

Articles from other publishers (47)

Rituparna Das & Balaram Mukhopadhyay. 2024. Synthetic Strategies in Carbohydrate Chemistry. Synthetic Strategies in Carbohydrate Chemistry 1 51 .
Marco Brito-AriasMarco Brito-Arias. 2022. Synthesis and Characterization of Glycosides. Synthesis and Characterization of Glycosides 1 100 .
Katarzyna Żurawska, Marcin Stokowy, Patryk Kapica, Monika Olesiejuk, Agnieszka Kudelko, Katarzyna Papaj, Magdalena Skonieczna, Wiesław Szeja, Krzysztof Walczak & Anna Kasprzycka. (2021) Synthesis and Preliminary Anticancer Activity Assessment of N-Glycosides of 2-Amino-1,3,4-thiadiazoles. Molecules 26:23, pages 7245.
Crossref
Chun‐Wei Chang, Mei‐Huei Lin & Cheng‐Chung Wang. (2020) Statistical Analysis of Glycosylation Reactions. Chemistry – A European Journal 27:8, pages 2556-2568.
Crossref
Chun‐Wei Chang, Chia‐Hui Wu, Mei‐Huei Lin, Pin‐Hsuan Liao, Chun‐Chi Chang, Hsiao‐Han Chuang, Su‐Ching Lin, Sarah Lam, Ved Prakash Verma, Chao‐Ping Hsu & Cheng‐Chung Wang. (2019) Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity. Angewandte Chemie International Edition 58:47, pages 16775-16779.
Crossref
Chun‐Wei Chang, Chia‐Hui Wu, Mei‐Huei Lin, Pin‐Hsuan Liao, Chun‐Chi Chang, Hsiao‐Han Chuang, Su‐Ching Lin, Sarah Lam, Ved Prakash Verma, Chao‐Ping Hsu & Cheng‐Chung Wang. (2019) Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity. Angewandte Chemie 131:47, pages 16931-16935.
Crossref
Haoxin Li, Allyson Bos, Stéphanie Jean, Duncan Webster, Gilles A. Robichaud, John A. Johnson & Christopher A. Gray. (2018) Antimycobacterial 1,4-napthoquinone natural products from Moneses uniflora. Phytochemistry Letters 27, pages 229-233.
Crossref
Aditya R. Pote, Raghu Vannam, Alissa Richard, José Gascón & Mark W. Peczuh. (2018) Formation of and Glycosylation with Per‐ O ‐Acetyl Septanosyl Halides: Rationalizing Complex Reactivity En Route to p ‐Nitrophenyl Septanosides . European Journal of Organic Chemistry 2018:14, pages 1709-1719.
Crossref
Vanessa Leiria Campo, Thalita B. Riul, Leandro Oliveira Bortot, Maristela B. Martins-Teixeira, Marcelo Fiori Marchiori, Emanuela Iaccarino, Menotti Ruvo, Marcelo Dias-Baruffi & Ivone Carvalho. (2017) A Synthetic MUC1 Glycopeptide Bearing βGalNAc-Thr as a Tn Antigen Isomer Induces the Production of Antibodies against Tumor Cells. ChemBioChem 18:6, pages 527-538.
Crossref
Matthew Schombs & Jacquelyn Gervay‐Hague. 2016. Glycochemical Synthesis. Glycochemical Synthesis 1 34 .
Rituparna Das & Balaram Mukhopadhyay. (2016) Chemical O-Glycosylations: An Overview. ChemistryOpen 5:5, pages 401-433.
Crossref
Hong Wang, Yanli Cui, Rong Zou, Zhaodong Cheng, Weirong Yao, Yangyi Mao & Yongmin Zhang. (2016) Synthesis of oligosaccharides using per-O-trimethylsilyl-glycosyl iodides as glycosyl donor. Carbohydrate Research 427, pages 1-5.
Crossref
A. Nikseresht. (2016) SnCl4: An efficient and inexpensive promoter for synthesis of ω-functionalized alkyl 1,2-trans-glycosides from 1-O-pivaloyl donor. Russian Journal of General Chemistry 86:1, pages 167-172.
Crossref
Ryszard B. Nazarski, Piotr Wałejko & Stanisław Witkowski. (2016) Multi-conformer molecules in solutions: an NMR-based DFT/MP2 conformational study of two glucopyranosides of a vitamin E model compound. Organic & Biomolecular Chemistry 14:11, pages 3142-3158.
Crossref
Marco Brito-AriasMarco Brito-Arias. 2016. Synthesis and Characterization of Glycosides. Synthesis and Characterization of Glycosides 1 79 .
Ryoichi Arihara, Kosuke Kakita, Noritoshi Suzuki, Seiichi Nakamura & Shunichi Hashimoto. (2015) Glycosylation with 2-Acetamido-2-deoxyglycosyl Donors at a Low Temperature: Scope of the Non-Oxazoline Method. The Journal of Organic Chemistry 80:9, pages 4259-4277.
Crossref
Santanu Jana, Madhu Emmadi & Suvarn S. Kulkarni. (2015) First Synthesis of the α‐ L ‐Serine Linked Consensus Disaccharide of Neisseria gonorrhoeae and Neisseria meningitidis . Israel Journal of Chemistry 55:3-4, pages 398-402.
Crossref
Vanessa L. Campo, Thalita B. Riul, Ivone Carvalho & Marcelo-Dias Baruffi. (2014) Antibodies against Mucin-Based Glycopeptides Affect Trypanosoma cruzi Cell Invasion and Tumor Cell Viability . ChemBioChem 15:10, pages 1495-1507.
Crossref
Hsiao‐Wu Hsieh, Ryan A. Davis, Jessica A. Hoch & Jacquelyn Gervay‐Hague. (2014) Two‐Step Functionalization of Oligosaccharides Using Glycosyl Iodide and Trimethylene Oxide and Its Applications to Multivalent Glycoconjugates. Chemistry – A European Journal 20:21, pages 6444-6454.
Crossref
Archanamayee Behera, Madhu Emmadi & Suvarn S. Kulkarni. (2014) Total synthesis of MECA-79. RSC Adv. 4:102, pages 58573-58580.
Crossref
Luciana Baldoni & Carla Marino. (2013) Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides. Carbohydrate Research 374, pages 75-81.
Crossref
Maristela B. Martins-Teixeira, Vanessa L. Campo, Monica Biondo, Renata Sesti-Costa, Zumira A. Carneiro, João S. Silva & Ivone Carvalho. (2013) α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi. Bioorganic & Medicinal Chemistry 21:7, pages 1978-1987.
Crossref
Samrat Dutta, Swarbhanu Sarkar, Shyam Ji Gupta & Asish Kumar Sen. (2013) Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donor in presence of thioglycosides. Tetrahedron Letters 54:8, pages 865-870.
Crossref
Kosuke Kakita, Toshifumi Tsuda, Noritoshi Suzuki, Seiichi Nakamura, Hisanori Nambu & Shunichi Hashimoto. (2012) A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures. Tetrahedron 68:25, pages 5005-5017.
Crossref
James T. Zacharia & Masahiko Hayashi. (2012) Facile synthesis of acacetin-7-O-β-d-galactopyranoside. Carbohydrate Research 348, pages 91-94.
Crossref
François-Moana Gautier, Florence Djedaïni-Pilard & Cyrille Grandjean. (2011) The iodosulfonamidation of peracetylated glycals revisited: access to 1,2-di-nitrogenated sugars. Carbohydrate Research 346:5, pages 577-587.
Crossref
Robert A. FieldPeterson AndradeVanessa L. CampoIvone CarvalhoBeatrice Y. M. ColletPaul R. CrockerMargherita FaisRositsa KaramanskaBalaram MukhopadhayaySergey A. NepogodievAbdul RashidMartin RejzekDavid A. RussellClaire L. SchofieldRenate M. van Well. 2011. Petite and Sweet: Glyco-Nanotechnology as a Bridge to New Medicines. Petite and Sweet: Glyco-Nanotechnology as a Bridge to New Medicines 143 159 .
Zbigniew J. Witczak. 2010. Carbohydrate Chemistry. Carbohydrate Chemistry 176 193 .
Michael De Castro & Cecilia H. Marzabadi. (2010) Preparation and reactions of iodo sugars. Tetrahedron 66:19, pages 3395-3404.
Crossref
Jia Lu Xue, Samy Cecioni, Li He, Sébastien Vidal & Jean-Pierre Praly. (2009) Variations on the SnCl4 and CF3CO2Ag-promoted glycosidation of sugar acetates: a direct, versatile and apparently simple method with either α or β stereocontrol. Carbohydrate Research 344:13, pages 1646-1653.
Crossref
Enoch A. Mensah & Hien M. Nguyen. (2009) Nickel-Catalyzed Stereoselective Formation of α-2-Deoxy-2-Amino Glycosides. Journal of the American Chemical Society 131:25, pages 8778-8780.
Crossref
Peter J. Meloncelli, Alan D. Martin & Todd L. Lowary. (2009) Glycosyl iodides. History and recent advances. Carbohydrate Research 344:9, pages 1110-1122.
Crossref
Akihiko Koizumi, Noriyasu Hada, Asuka Kaburaki, Kimiaki Yamano, Frank Schweizer & Tadahiro Takeda. (2009) Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcusmultilocularis. Carbohydrate Research 344:7, pages 856-868.
Crossref
Aslan Esmurziev, Nebojša Simić, Eirik Sundby & Bård Helge Hoff. (2009) 1 H and 13 C NMR data of methyl tetra- O -benzoyl- D -pyranosides in acetone- d 6 . Magnetic Resonance in Chemistry 47:5, pages 449-452.
Crossref
Xiangming Zhu & Richard R. Schmidt. (2009) New Principles for Glycoside-Bond Formation. Angewandte Chemie International Edition 48:11, pages 1900-1934.
Crossref
Xiangming Zhu & Richard R. Schmidt. (2009) Neue Prinzipien für die Bildung von glycosidischen Bindungen. Angewandte Chemie 121:11, pages 1932-1967.
Crossref
Robert V. Stick & Spencer J. Williams. 2009. Carbohydrates: The Essential Molecules of Life. Carbohydrates: The Essential Molecules of Life 133 202 .
Teiichi Murakami, Yukari Sato & Motonari Shibakami. (2008) Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters. Carbohydrate Research 343:8, pages 1297-1308.
Crossref
Wiesław Szeja, Grzegorz Grynkiewicz & Robert A. Field. 2008. Handbook of Chemical Glycosylation. Handbook of Chemical Glycosylation 329 379 .
Shin‐Ichiro Shoda, Suvarn S. Kulkarni & Jacquelyn Gervay‐Hague. 2008. Handbook of Chemical Glycosylation. Handbook of Chemical Glycosylation 29 93 .
José Antonio Morales-Serna, Yolanda Díaz, M. Isabel Matheu & Sergio Castillón. (2008) Stannyl ceramides as efficient acceptors for synthesising β-galactosyl ceramides. Organic & Biomolecular Chemistry 6:20, pages 3831.
Crossref
Zerong Daniel Wang, Samia O. Sheikh, Shannon Cox, Yulu Zhang & Keegan Massey. (2007) Direct Preparation of N-Glycosidic Bond-Linked Nonionic Carbohydrate-Based Surfactant (NICBS) via Ritter Reaction. European Journal of Organic Chemistry 2007:14, pages 2243-2247.
Crossref
Vanessa Leiria Campo, Ivone Carvalho, Sarah Allman, Benjamin G. Davis & Robert A. Field. (2007) Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins. Organic & Biomolecular Chemistry 5:16, pages 2645.
Crossref
. 2007. Synthesis and Characterization of Glycosides. Synthesis and Characterization of Glycosides 1 67 .
Qian Wan, Jiehao Chen, Gong Chen & Samuel J. Danishefsky. (2006) A Potentially Valuable Advance in the Synthesis of Carbohydrate-Based Anticancer Vaccines through Extended Cycloaddition Chemistry. The Journal of Organic Chemistry 71:21, pages 8244-8249.
Crossref
Renate M. van Well, Tiina S. Kärkkäinen, K.P. Ravindranathan Kartha & Robert A. Field. (2006) Contrasting reactivity of thioglucoside and selenoglucoside donors towards promoters: implications for glycosylation stereocontrol. Carbohydrate Research 341:10, pages 1391-1397.
Crossref
Renate M. van Well, K. P. Ravindranathan Kartha & Robert A. Field. (2005) Iodine Promoted Glycosylation with Glycosyl Iodides: α‐Glycoside Synthesis.. ChemInform 36:52.
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:

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:

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.