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Stereoselective Synthesis of 2‐Deoxyglycosides from Sulfanyl Alkenes by Consecutive “One Pot” Cyclization and Glycosylation Reactions
Author(s) -
Rodríguez Miguel A.,
Boutureira Omar,
Matheu M. Isabel,
Díaz Yolanda,
Castillón Sergio
Publication year - 2007
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.200601115
Subject(s) - chemistry , sulfanyl , glycosylation , stereoselectivity , one pot synthesis , organic chemistry , stereochemistry , catalysis , biochemistry
2‐Deoxy‐2‐iodopyranosides 3 , and 9 – 12 were synthesized from sulfanyl alkenes using a “one pot” consecutive cyclization–glycosylation process. Compared with the stepwise procedure, the “one pot” process gave significantly improved yields with similar or slightly lower selectivities. The “onepot” procedure was applied to the synthesis of 2,6‐dideoxy‐2‐iodoglycoside 22 , which was successfully deiodinated to afford the 2,6‐dideoxyglycoside 23 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)