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Rapid Synthesis of l ‐Idosyl Glycosyl Donors from α‐Thioglucosides for the Preparation of Heparin Disaccharides
Author(s) -
Herczeg Mihály,
Demeter Fruzsina,
Balogh Tímea,
Kelemen Viktor,
Borbás Anikó
Publication year - 2018
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.201800425
Subject(s) - chemistry , hydroboration , glycosyl , glycosylation , epimer , glycosyl donor , stereoselectivity , stereochemistry , substituent , acetal , anomer , heparin , protecting group , total synthesis , organic chemistry , biochemistry , catalysis , alkyl
A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l ‐idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6‐acetal formation. The α‐anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l ‐ ido diastereoselectivity. The 4,6‐arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α‐idosylation could be achieved by using idosyl donors without a C‐2 participating group.