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An Efficient Synthesis of ( R )‐3‐{( R )‐3‐[2‐ O ‐(α‐L‐Rhamnopyranosyl)‐ α‐L‐rhamnopyranosyl] oxydecanoyl}oxydecanoic Acid, a Rhamnolipid from Pseudomonas Aeruginosa
Author(s) -
Duynstee Howard I.,
van Vliet Michiel J.,
van der Marel Gijsbert A.,
van Boom Jacques H.
Publication year - 1998
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/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u
Subject(s) - chemistry , rhamnolipid , diazomethane , thio , derivative (finance) , glycosylation , stereochemistry , glycoside , organic chemistry , bacteria , pseudomonas aeruginosa , biochemistry , genetics , biology , financial economics , economics
N ‐iodosuccinimide/triflic acid mediated one‐pot two‐step glycosylation of ethyl 2,3,4‐tri‐ O ‐benzyl‐1‐thio‐α‐L‐rhamnopyranoside ( 8 ) with phenyl 3,4‐ O ‐(2,3‐dimethoxybutane‐2,3‐diyl)‐1‐thio‐α‐L‐rhamnopyranoside ( 10b ) and phenacyl ( R )‐3‐hydroxydecanoate ( 13 ) gave rhamnolipid 17 . The latter was transformed in five steps into the title compound 2 . Esterification of 2 with diazomethane resulted into the corresponding methyl ester derivative 1 .