Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of a glycosphingolipid analogue from the parasite Spirometra erinacei.

Abstract:

:Novel neutral glycosphingolipids isolated from the plerocercoids of a tapeworm, Spirometra erinacei, may be expected to be involved in host-parasite interactions. We have synthesized this glycosphingolipid analogue containing 2-branched fatty alkyl residue in place of ceramide. Glycosylation of nonreducing-end trisaccharide derivative 15 with the reducing-end disaccharide derivative 17 in the presence of trimethylsilyl triflate (TMSOTf) gave the desired oligosaccharide derivative in good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycoside 19 was converted to glycosylimidate 20, which was condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated to give the target glycosphingolipid analogue 22.

authors

Hada N,Kuroda M,Takeda T

doi

10.1248/cpb.48.1160

subject

Has Abstract

pub_date

2000-08-01 00:00:00

pages

1160-5

issue

8

eissn

0009-2363

issn

1347-5223

journal_volume

48

pub_type

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