Synthesis of oligosaccharides designed to form micelles, corresponding to structures found in ovarian cyst fluid

Article abstract of DOI:10.1080/07328300008544063

The syntheses of α-D-GlcpNAc-(1 →4)-β-D-Galp-(1→4)-β-D-GlcNAc-(1→O)-(CH₂)₁₅CH₃ (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromoderivative 18. For the synthesis of disaccharide β-D-Galp-(1 →4)-D-GlcNAc, several differently protected glucosamine acceptors were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the β-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1 →4)-2,3,6-tri-O-benzoyl-α-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.

Full text of DOI:10.1080/07328300008544063

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Journal of Carbohydrate Chemistry
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Synthesis of Oligosaccharides
Designed to form Micelles,
Corresponding to Structures Found
in Ovarian Cyst Fluid
Therese Buskas & Peter Konradsson
a Department of Organic Chemistry, , Arrhenius Laboratory,
Stockholm University , S-106 91 Stockholm, Sweden
b Department of Organic Chemistry, , Arrhenius Laboratory,
Stockholm University , S-106 91 Stockholm, Sweden
Published online: 27 Feb 2008.
To cite this article: Therese Buskas & Peter Konradsson (2000) Synthesis of Oligosaccharides
Designed to form Micelles, Corresponding to Structures Found in Ovarian Cyst Fluid, Journal of
Carbohydrate Chemistry, 19:1, 25-51, DOI: 10.1080/07328300008544063
To link to this article: http://dx.doi.org/10.1080/07328300008544063
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