Asymmetric synthesis of alkane- and arenesulfinates of diacetone-D-glucose (DAG): an improved and general route to both enantiomerically pure sulfoxides

1992 ◽  
Vol 57 (25) ◽  
pp. 6789-6796 ◽  
Author(s):  
I. Fernandez ◽  
N. Khiar ◽  
J. M. Llera ◽  
F. Alcudia
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomerically Pure

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.

Asymmetric synthesis of enantiomerically pure 7-isopropenyl-4a-methyl-3-methyleneoctahydrochromen-2-ones

2007 ◽  
Vol 18 (22) ◽  
pp. 2712-2718 ◽  
Author(s):  
Henryk Krawczyk ◽  
Marcin Śliwiński ◽  
Jacek Kędzia ◽  
Jakub Wojciechowski ◽  
Wojciech M. Wolf
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomerically Pure
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