Premium
Reaction of Glycals with Organic Peroxides: Synthesis of 2‐iodo, 2‐Deoxy and 2,3‐Unsaturated Glycosides
Author(s) -
Rasool Faheem,
Bhat Aabid H.,
Hussain Nazar,
Mukherjee Debaraj
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601849
Subject(s) - chemistry , glycal , glycoside , glycosylation , catalysis , organic chemistry , decomposition , selectivity , alcohol , biochemistry , stereoselectivity
Reaction of peroxides with glycals, when carried in the presence of NIS affords2‐deoxy‐2‐iodo‐α‐glycosides in good yields with predominant trans‐diaxial selectivity at rt. Under photolytic conditions in the presence of catalytic eosin Y, the reaction leads to 2‐deoxyglycosides or 2,3‐unsaturated‐α‐glycosides. NIS plays two roles firstly, to form an iodonium ion with the glycal and secondly to bring about the decomposition of the organic peroxide into an alcohol that reacts with the activated sugar whereas blue LED light and Eosin Y bring about a radical‐mediated glycosylation to give the α‐2‐deoxy glycoside or 2,3‐unsaturated glycosides based on the protecting group at C‐3 position of glycals.