Advanced search
Publication Cover
Journal of Carbohydrate Chemistry Volume 23, 2004 - Issue 6-7
Submit an article Journal homepage
223
Views
38
CrossRef citations to date
0
Altmetric
Original Articles

Zirconium(IV) Chloride Catalyzed Synthesis of 2,3‐Unsaturated C, N, O, S, and Heteroaromatic Glycosylation in the Ferrier Rearrangement

Navath Raghavendra Swamy Organic Chemistry Division‐I, Natural Product Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
Masuna Srinivasulu Organic Chemistry Division‐I, Natural Product Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
Thummalapally Srikanth Reddy Organic Chemistry Division‐I, Natural Product Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
Thirumani Venkateshwar Goud Organic Chemistry Division‐I, Natural Product Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
&
Yenamandra Venkateswarlu Organic Chemistry Division‐I, Natural Product Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, IndiaCorrespondence[email protected]
Pages 435-441 | Received 12 Jul 2004, Accepted 20 Jul 2004, Published online: 18 Aug 2006

Citations (38)

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 (1)

Qiang Tian, Xing‐Mei Zhu & Jin‐Song Yang. (2007) Amberlyst 15–Catalyzed Efficient Synthesis of 2,3‐Unsaturated Glycosides via Ferrier Rearrangement for Glycal. Synthetic Communications 37:5, pages 691-701.
Read now

Articles from other publishers (37)

Aparna Das, Ram Naresh Yadav & Bimal Krishna Banik. (2023) Conceptual design and cost-efficient environmentally Benign synthesis of beta-lactams. Physical Sciences Reviews 8:11, pages 4053-4084.
Crossref
Anand GauravZanjila AzeemPintu Kumar Mandal. (2023) Tris(pentafluorophenyl)borane-Catalyzed Stereoselective C-Glycosylation of Glycals: A Facile Synthesis of Allyl and Alkynyl Glycosides. Synthesis.
Crossref
Vidya Jose, Elizabeth J. Diana, U.S. Kanchana & Thomas V. Mathew. (2023) Current trends and advancements in Ferrier and Petasis-Ferrier rearrangement. Journal of Organometallic Chemistry 991, pages 122691.
Crossref
Sonali Priyadarshini Parida, Tapaswini Das, Mohammed Ansar Ahemad, Tapaswini Pati, Seetaram Mohapatra & Sabita Nayak. (2023) Recent advances on synthesis of C-glycosides. Carbohydrate Research, pages 108856.
Crossref
Rupa Bai Addanki, Suvendu Halder & Pavan K. Kancharla. (2022) TfO – ···H–O–H Interaction-Assisted Generation of a Silicon Cation from Allylsilanes: Access to Phenylallyl Ferrier Glycosides from Glycals . Organic Letters 24:7, pages 1465-1470.
Crossref
P.I. Ramesh, Mohamad Saif Ali, Subhash Ghosh & Madhu Babu Tatina. (2022) Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement. Results in Chemistry 4, pages 100347.
Crossref
Naresh Bhuma, Ludivine Lebedel, Hiroki Yamashita, Yutaka Shimizu, Zahra Abada, Ana Ardá, Jérôme Désiré, Bastien Michelet, Agnès Martin‐Mingot, Ali Abou‐Hassan, Masahiro Takumi, Jérôme Marrot, Jesús Jiménez‐Barbero, Aiichiro Nagaki, Yves Blériot & Sébastien Thibaudeau. (2020) Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids. Angewandte Chemie International Edition 60:4, pages 2036-2041.
Crossref
Naresh Bhuma, Ludivine Lebedel, Hiroki Yamashita, Yutaka Shimizu, Zahra Abada, Ana Ardá, Jérôme Désiré, Bastien Michelet, Agnès Martin‐Mingot, Ali Abou‐Hassan, Masahiro Takumi, Jérôme Marrot, Jesús Jiménez‐Barbero, Aiichiro Nagaki, Yves Blériot & Sébastien Thibaudeau. (2020) Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids. Angewandte Chemie 133:4, pages 2064-2069.
Crossref
Károly Ágoston & Gregory M. Watt. 2021. Comprehensive Glycoscience. Comprehensive Glycoscience 103 159 .
Nan Jiang, Zhengliang Wu, Youxian Dong, Xiaoxia Xu, Xiaxia Liu & Jianbo Zhang. (2020) Progress in the Synthesis of 2,3-unsaturated Glycosides. Current Organic Chemistry 24:2, pages 184-199.
Crossref
Umesh P. Aher, Dhananjai Srivastava, Harishchandra S. Jadhav, Girij P. Singh, Jayashree B. S. & Gautham G. Shenoy. (2020) Large-Scale Stereoselective Synthesis of 1,3-Oxathiolane Nucleoside, Lamivudine, via ZrCl 4 -Mediated N -Glycosylation . Organic Process Research & Development 24:3, pages 387-397.
Crossref
Kei Kitamura, Yoshio Ando, Takashi Matsumoto & Keisuke Suzuki. (2017) Total Synthesis of Aryl C -Glycoside Natural Products: Strategies and Tactics . Chemical Reviews 118:4, pages 1495-1598.
Crossref
Silvia Miranda, Fernando Lobo, Ana M. Gomez & J. Cristobal Lopez. (2017) Ferrier-Nicholas Cations from C-3-Alkynylglycals: Access to C-3-Branched Allylic Glycosides and Ring-Opening Derivatives. European Journal of Organic Chemistry 2017:17, pages 2501-2511.
Crossref
Éva Bokor, Sándor Kun, David Goyard, Marietta Tóth, Jean-Pierre Praly, Sébastien Vidal & László Somsák. (2017) C -Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential . Chemical Reviews 117:3, pages 1687-1764.
Crossref
Xiaohua Li & Jianglong Zhu. (2016) Glycosylation via Transition-Metal Catalysis: Challenges and Opportunities. European Journal of Organic Chemistry 2016:28, pages 4724-4767.
Crossref
Peiran Chen & Jie Su. (2016) Gd(OTf) 3 catalyzed preparation of 2,3-unsaturated O -, S -, N -, and C -pyranosides from glycals by Ferrier Rearrangement. Tetrahedron 72:1, pages 84-94.
Crossref
Agnieszka Kubiak, Robert Kołodziuk, Stanisław Porwański & Anna Zawisza. (2015) Palladium(0)-catalysed synthesis of 2,3- and 3,4-unsaturated aryl β-O-glycosides. Carbohydrate Research 417, pages 34-40.
Crossref
Peiran Chen & Bin Bi. (2015) Preparation of 2,3-unsaturated pseudoglycosides with Ferrier Rearrangement promoted by Tm(OTf)3 as a highly efficient catalyst. Tetrahedron Letters 56:34, pages 4895-4899.
Crossref
Yen-Bo Chen, Su-I. Wang, Zi-Ping Lin, Chun-Hung Lin, Min-Tsang Hsieh & Hui-Chang Lin. (2015) Stereoselective glycosylation of d-galactals by diethyl phosphorochloridite- and AlCl3-assisted Ferrier rearrangement. Tetrahedron 71:2, pages 350-358.
Crossref
Peiran Chen & Dalin Zhang. (2014) Sm(OTf)3 as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals. Tetrahedron 70:45, pages 8505-8510.
Crossref
Peiran Chen & Shan Li. (2014) Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides. Tetrahedron Letters 55:42, pages 5813-5816.
Crossref
Rashmi Roy, Parasuraman Rajasekaran, Asadulla Mallick & Yashwant D. Vankar. (2014) Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O ‐Glycosylation of 1‐ O ‐Acetyl Sugars as Glycosyl Donors . European Journal of Organic Chemistry 2014:25, pages 5564-5573.
Crossref
Peiran Chen & Lei Lin. (2013) RuCl3·3H2O as catalyst for Ferrier rearrangement: an efficient procedure for the preparation of pseudoglycosides. Tetrahedron 69:47, pages 10045-10051.
Crossref
Ana M. Gómez, Fernando Lobo, Clara Uriel & J. Cristóbal López. (2013) Recent Developments in the Ferrier Rearrangement. European Journal of Organic Chemistry 2013:32, pages 7221-7262.
Crossref
Peiran Chen & Lei Lin. (2013) An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type I Ferrier rearrangement. Tetrahedron 69:23, pages 4524-4531.
Crossref
Peiran Chen & Shaoshan Wang. (2013) CF3SO3H–SiO2 as catalyst for Ferrier rearrangement: an efficient procedure for the synthesis of pseudoglycosides. Tetrahedron 69:2, pages 583-588.
Crossref
Dragana Stevanović, Anka Pejović, Ivan Damljanović, Mirjana Vukićević, Goran A. Bogdanović & Rastko D. Vukićević. (2012) Anodic generation of a zirconium catalyst for Ferrier rearrangement and hetero Michael addition. Tetrahedron Letters 53:46, pages 6257-6260.
Crossref
Peiran Chen & Shaoshan Wang. (2012) Iron(III) triflate, a new efficient catalyst for Type I Ferrier Rearrangement. Tetrahedron 68:27-28, pages 5356-5362.
Crossref
Goutam Guchhait & Anup Kumar Misra. (2011) Environmentally Benign Synthesis of 2,3-Unsaturated Glycopyranosides in Task-Specific Ionic Liquid. Catalysis Letters 141:7, pages 925-930.
Crossref
Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 1046 1050 .
Pieter Levecque, David W. Gammon, Pierre Jacobs, Dirk De Vos & Bert Sels. (2010) The use of ultrastable Y zeolites in the Ferrier rearrangement of acetylated and benzylated glycals. Green Chemistry 12:5, pages 828.
Crossref
Todd A. Houston & Masato Koreeda. (2009) Iodine-promoted ribosylation leads to a facile acetonide-forming reaction. Carbohydrate Research 344:16, pages 2240-2244.
Crossref
Paramathevar Nagaraj & Namakkal G. Ramesh. (2009) Direct Ferrier rearrangement on unactivated glycals catalyzed by indium(III) chloride. Tetrahedron Letters 50:27, pages 3970-3973.
Crossref
Amélia P. Rauter, Tânia Almeida, Nuno M. Xavier, Filipa Siopa, Ana I. Vicente, Susana D. Lucas, João P. Marques, Fernando Ramôa Ribeiro, Michel Guisnet & Maria J. Ferreira. (2007) Acid zeolites as efficient catalysts for O- and S-glycosylation. Journal of Molecular Catalysis A: Chemical 275:1-2, pages 206-213.
Crossref
K. Toshima & K. Sasaki. 2007. Comprehensive Glycoscience. Comprehensive Glycoscience 261 311 .
Lise-Lotte Gundersen, Frode Rise, Kjell Undheim & Yvan Le Huérou. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Navath Raghavendra Swamy, Masuna Srinivasulu, Thummalapally Srikanth Reddy, Thirumani Venkateshwar Goud & Yenamandra Venkateswarlu. (2005) Zirconium(IV) Chloride Catalyzed Synthesis of 2,3‐Unsaturated C, N, O, S, and Heteroaromatic Glycosylation in the Ferrier Rearrangement.. ChemInform 36:21.
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.