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Synthesis of Potassium (2 R )‐2‐ O ‐α‐ D ‐Mannopyranosyl‐(1→2)‐α‐ D ‐glucopyranosyl‐2,3‐dihydroxypropanoate: A Naturally Compatible Solute
Author(s) -
Lourenço Eva C.,
Ventura M. Rita
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100934
Subject(s) - chemistry , glycosylation , stereochemistry , acetal , potassium , glycosyl donor , anomer , derivative (finance) , disaccharide , salt (chemistry) , glycoside , organic chemistry , biochemistry , financial economics , economics
An expedient synthesis of the potassium salt of (2 R )‐2‐ O ‐α‐ D ‐mannopyranosyl‐(1→2)‐α‐ D ‐glucopyranosyl‐2,3‐dihydroxypropanoic acid (MGG)―a recently isolated, rare, compatible solute―was accomplished. A bis‐acetal‐protected thioglucoside, 6‐OTBDPS, with a 2‐OH group was used as the acceptor in the first glycosylation reaction with tetraacetylmannosyl trichloroacetimidate, and as the donor in the glycosylation reaction with the glycerate derivative. The α anomer was the only product of both glycosylation reactions, as expected for the formation of the α‐mannoside. The formation of the 1,2‐ cis glucoside was more challenging.