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Literature DB >> 23646882

Selective synthesis of 1,2-cis-α-glycosides without directing groups. Application to iterative oligosaccharide synthesis.

An-Hsiang Adam Chu¹, Son Hong Nguyen, Jordan A Sisel, Andrei Minciunescu, Clay S Bennett.

Abstract

A method for the highly selective synthesis of 1,2-cis-α-linked glycosides that does not require the use of the specialized protecting group patterns normally employed to control diastereoselectivity is described. Thioglycoside acceptors can be used, permitting iterative oligosaccharide synthesis. The approach eliminates the need for lengthy syntheses of monosaccharides possessing highly specialized and unconventional protecting group patterns.

Entities: Chemical

Mesh：

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Year: 2013 PMID： 23646882 DOI： 10.1021/ol401095k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

12 in total

1. Pre-activation Based Stereoselective Glycosylations.

Authors: Bo Yang; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal: European J Org Chem Date: 2017-12-28

2. Regenerative glycosylation under nucleophilic catalysis.

Authors: Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal: J Am Chem Soc Date: 2014-01-09 Impact factor: 15.419

3. Mapping the Reactivity and Selectivity of 2-Azidofucosyl Donors for the Assembly of N-Acetylfucosamine-Containing Bacterial Oligosaccharides.

Authors: Bas Hagen; Sara Ali; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal: J Org Chem Date: 2017-01-10 Impact factor: 4.354

Review 4. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors: Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal: Chem Rev Date: 2022-06-08 Impact factor: 72.087

Selective synthesis of 1,2-cis-α-glycosides without directing groups. Application to iterative oligosaccharide synthesis.

1. Pre-activation Based Stereoselective Glycosylations.

2. Regenerative glycosylation under nucleophilic catalysis.

3. Mapping the Reactivity and Selectivity of 2-Azidofucosyl Donors for the Assembly of N-Acetylfucosamine-Containing Bacterial Oligosaccharides.

Review 4. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Review 5. Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Review 6. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

7. Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

8. A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors.

9. An air- and water-stable iodonium salt promoter for facile thioglycoside activation.

10. Reagent Controlled Stereoselective Synthesis of α-Glucans.