✦ LIBER ✦

Synthesis and conformation of 1,2-anhydro,3,4-6-tri-O-benzyl-β-d-talopyranose

✍ Scribed by Jianhui Liu; Fanzuo Kong; Lingxiao Cao

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 403 KB
Volume: 240
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84192-9

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✦ Synopsis

1,2-Anhydro sugar derivatives are important intermediates for the synthesis of oligosaccharides' and polysaccharides2, and also for chemical modification of monosaccharides3. The synthesis of I,2-anhydro-o-manno-4, -o-gluco-5, and -D-galactopyranose6 derivatives by an intramolecular S,2 reaction of a free hydroxyl group on C-2 with C-l bearing a leaving group have been reported. Recently' a new method for the synthesis of l,Zanhydro-a-o-gluco-and -galactopyranose derivatives by direct epoxidation of the corresponding glycals was described','. It seemed, however, to be difficult to prepare 1,2_anhydropyranose compounds with a 3-hydroxy group cis-arranged to the epoxide ring by the new method. Thus the traditional method by an intramolecular S,2 reaction still retains its merit. Herein we report the synthesis and conformational analysis of 1,2-anhydro-3,4,6-tri-o-ben-zyl+-o-talopyranose by both iH NMR spectrometry and MMP2 methods.

Methyl 6-0-benzoyl-2,3-0-isopropylidene-a-D-talopyranoside

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