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Synthesis of beta-C-galactosyl D- and L-alanines

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Title Synthesis of beta-C-galactosyl D- and L-alanines
 
Creator THOTA, VN
GERVAY-HAGUE, J
KULKARNI, SS
 
Subject GLYCOSYL AMINO-ACIDS
STEREOSELECTIVE-SYNTHESIS
ARTIFICIAL GLYCOPEPTIDES
GENERAL-SYNTHESIS
RADICAL-ADDITION
ALCOHOLS
ROUTE
TETRAHYDROFURANS
FURANOSIDES
CYCLIZATION
 
Description Synthesis of beta-C-D-galactosyl D- and L-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and S(N)2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-10-14T13:37:50Z
2014-10-14T13:37:50Z
2012
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 10(40)8132-8139
http://dx.doi.org/10.1039/c2ob26078f
http://dspace.library.iitb.ac.in/jspui/handle/100/14519
 
Language en