Recent Development of Stereoselective Glycosylation Reactions

Heterocycles ◽  
2021 ◽  
Vol 102 (2) ◽  
pp. 177
Author(s):  
Shino Manabe
Keyword(s):  
Stereoselective Glycosylation

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

scholarly journals Stereoselective synthesis of glycosides using (salen)Co catalysts as promoters

2015 ◽  
Vol 51 (43) ◽  
pp. 8939-8941 ◽  
Author(s):  
Sandra Medina ◽  
Alexander S. Henderson ◽  
John F. Bower ◽  
M. Carmen Galan
Keyword(s):  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Co Catalysts ◽  
New Class ◽  
Stereoselective Glycosylation ◽  
Glycosyl Donors

The use of (salen)Co catalysts as a new class of bench-stable stereoselective glycosylation promoters of trichloroacetimidate glycosyl donors at room temperature is described.

A Convergent Total Synthesis of the Mucin Related F1αAntigen by One-Pot Sequential Stereoselective Glycosylation

2001 ◽  
Vol 30 (8) ◽  
pp. 840-841 ◽  
Author(s):  
Teruaki Mukaiyama ◽  
Kazuhiro Ikegai ◽  
Hideki Jona ◽  
Takashi Hashihayata ◽  
Kazuya Takeuchi
Keyword(s):  
Total Synthesis ◽  
One Pot ◽  
Stereoselective Glycosylation

Stereoselective Glycosylation Reactions with Chiral Auxiliaries

2005 ◽  
Vol 44 (6) ◽  
pp. 947-949 ◽  
Author(s):  
Jin-Hwan Kim ◽  
Hai Yang ◽  
Geert-Jan Boons
Keyword(s):  
Chiral Auxiliaries ◽  
Stereoselective Glycosylation

Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst

2015 ◽  
Vol 54 (37) ◽  
pp. 10935-10939 ◽  
Author(s):  
Akira Nakagawa ◽  
Masamichi Tanaka ◽  
Shun Hanamura ◽  
Daisuke Takahashi ◽  
Kazunobu Toshima
Keyword(s):  
Stereoselective Glycosylation ◽  
Boronic Ester

Boronic-Acid-Catalyzed Regioselective and 1,2-cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via SNi-Type Mechanism

2018 ◽  
Vol 140 (10) ◽  
pp. 3644-3651 ◽  
Author(s):  
Masamichi Tanaka ◽  
Akira Nakagawa ◽  
Nobuya Nishi ◽  
Kiyoko Iijima ◽  
Ryuichi Sawa ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Stereoselective Glycosylation ◽  
Acid Catalyzed
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