Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Highly Direct alpha-Selective Glycosylations of 3,4-O-Carbonate-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol.

Literature DB >> 18630923

Highly Direct alpha-Selective Glycosylations of 3,4-O-Carbonate-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol.

Yin-Suo Lu¹, Qin Li, Li-He Zhang, Xin-Shan Ye.

Abstract

A new efficient pre-activation method for the highly alpha-stereoselective glycosylation of 2-deoxysugars and 2,6-dideoxysugars has been developed using 2-deoxy- and 2,6-dideoxythioglycosides as glycosyl donors. The approach allows a wide range of glycosyl acceptors and donors to be used; the alpha-selectivity is very good to excellent.

Entities: Chemical

Mesh：

Substances：
Carbonates
Thioglycosides

Year: 2008 PMID： 18630923 DOI： 10.1021/ol801190c

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

Keyword Cloud
Cited

13 in total

Review 1. Methods for 2-Deoxyglycoside Synthesis.

Authors: Clay S Bennett; M Carmen Galan
Journal: Chem Rev Date: 2018-06-28 Impact factor: 60.622

Review 2. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors: Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal: Chem Rev Date: 2018-06-28 Impact factor: 60.622

3. Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

Authors: Youlin Zeng; Zhen Wang; Dennis Whitfield; Xuefei Huang
Journal: J Org Chem Date: 2008-09-23 Impact factor: 4.354

Highly Direct alpha-Selective Glycosylations of 3,4-O-Carbonate-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol.

Review 1. Methods for 2-Deoxyglycoside Synthesis.

Review 2. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

3. Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

4. Pre-activation Based Stereoselective Glycosylations.

5. Recent Advances in Transition Metal-Catalyzed Glycosylation.

6. An efficient and cost-effective preparation of di-O-acetyl-D-rhamnal.

7. Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit.

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

Review 9. Chemical O-Glycosylations: An Overview.

10. Synthetic Carbohydrate Chemistry and Translational Medicine.