Open AccessSynthesis of the Tolerance‐Inducing Oligosaccharide Lacto‐ N ‐Fucopentaose III Bearing an Activated Linker
Author(s) -
Zhang Junfeng,
Zou Lu,
Lowary Todd L.
Publication year - 2013
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201300024
Subject(s) - linker , chemistry , aglycone , disaccharide , conjugate , oligosaccharide , stereoselectivity , total synthesis , stereochemistry , alkene , combinatorial chemistry , organic chemistry , glycoside , catalysis , computer science , mathematical analysis , mathematics , operating system
A concise synthetic route to an immunomodulatory pentasaccharide, lacto‐ N ‐fucopentaose III ( 1 ) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio‐ and stereoselective glycosylations for the construction of disaccharide 10 and pentasaccharide 12 , a Birch reduction for deprotection of benzyl ethers, and a UV‐promoted radical addition of a thiol to an alkene for modification of the aglycone.