An Efficient Synthesis of (R)-3-{(R)-3-[2-O-(α-L-Rhamnopyranosyl)- α-L-rhamnopyranosyl] oxydecanoyl}oxydecanoic Acid, a Rhamnolipid from Pseudomonas Aeruginosa
✍ Scribed by Howard I. Duynstee; Michiel J. van Vliet; Gijsbert A. van der Marel; Jacques H. van Boom
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 478 KB
- Volume
- 1998
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Pseudomonas aeruginosa / Rhamnolipid / One-pot two-step glycosylation / Chemoselectivity / Esterification / Carbohydrates N-iodosuccinimide/triflic acid mediated one-pot two-step hydroxydecanoate (13) gave rhamnolipid 17. The latter was transformed in five steps into the title compound 2. 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-Esterification of 2 with diazomethane resulted into the corresponding methyl ester derivative 1. diyl)-1-thio-α-L-rhamnopyranoside (10b) and phenacyl (R)-3-