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Literature DB >> 20692651

Activation of glycosyl trichloroacetimidates with perchloric acid on silica (HClO(4)-SiO(2)) provides enhanced alpha-selectivity.

Olaf R Ludek¹, Wenlu Gu, Jeffrey C Gildersleeve.

Abstract

Obtaining high stereoselectivity in glycosylation reactions is often challenging in the absence of neighboring group participation. In this study, we demonstrate that activation of glycosyl trichloroacetimidate donors with immobilized perchloric acid on silica (HClO(4)-SiO(2)) provides higher alpha-selectivity than trimethylsilyl triflate (TMSOTf) for reactions that do not involve neighboring group participation. Published by Elsevier Ltd.

Entities: Chemical Disease Gene Species

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Year: 2010 PMID： 20692651 PMCID： PMC2933952 DOI： 10.1016/j.carres.2010.07.030

Source DB: PubMed Journal: Carbohydr Res ISSN： 0008-6215 Impact factor: 2.104

19 in total

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2. Chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant.

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Review 3. Chemical glycobiology.

Authors: C R Bertozzi; L L Kiessling
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Review 4. Applications of synthetic carbohydrates to chemical biology.

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Journal: Curr Opin Chem Biol Date: 2010-03-12 Impact factor: 8.822

5. Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel.

Authors: Aditi Agarwal; Yashwant D Vankar
Journal: Carbohydr Res Date: 2005-07-04 Impact factor: 2.104

6. Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals.

Authors: Aditi Agarwal; Shikha Rani; Yashwant D Vankar
Journal: J Org Chem Date: 2004-09-03 Impact factor: 4.354

7. Cowpea mosaic virus capsid: a promising carrier for the development of carbohydrate based antitumor vaccines.

Authors: Adeline Miermont; Hannah Barnhill; Erica Strable; Xiaowei Lu; Katherine A Wall; Qian Wang; M G Finn; Xuefei Huang
Journal: Chemistry Date: 2008 Impact factor: 5.236

Review 8. Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research.

Authors: Thomas J Boltje; Therese Buskas; Geert-Jan Boons
Journal: Nat Chem Date: 2009-11 Impact factor: 24.427

9. From solution phase to "on-column" chemistry: trichloroacetimidate-based glycosylation promoted by perchloric acid-silica.

Authors: Balaram Mukhopadhyay; Sarah V Maurer; Nadine Rudolph; Renate M van Well; David A Russell; Robert A Field
Journal: J Org Chem Date: 2005-10-28 Impact factor: 4.354