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New Synthesis of 1‐ D ‐ O ‐(2‐Amino‐2‐deoxy‐ D ‐gluco‐ and ‐galactopyranosyl)‐ chiro ‐inositols
Author(s) -
Cid M. Belén,
Bonilla Julia B.,
Dumarçay Stéphane,
Alfonso Francisco,
MartínLomas Manuel
Publication year - 2002
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 - 10.1002/1099-0690(200203)2002:5<881::aid-ejoc881>3.0.co;2-z
Subject(s) - chemistry , vicinal , glycosylation , stereochemistry , diol , molecule , inositol , combinatorial chemistry , organic chemistry , biochemistry , receptor
New and highly effective procedures for the preparation of D ‐ chiro ‐inositol derivatives, essentially based on selective protection of the vicinal diequatorial diol systems present in this molecule, are reported. This selective protection affords C 2 ‐symmetric diaxial diols such as 4 and 5 , glycosylation of which under different conditions has been investigated. This study has provided a ready and convenient route to structures such as III − V , containing some of the structural motifs thought to be present in putative inositolphosphoglycan insulin mediators.