A convenient synthesis of pyranosyl-1-carbaldoximes

K W J  Baker; A  Gibb; A R  March; S  Parsons; R M  Paton

doi:10.1081/SCC-120018932

A convenient synthesis of pyranosyl-1-carbaldoximes

K W J Baker, A Gibb, A R March, S Parsons, R M Paton

School of Chemistry

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Abstract

A simple high-yielding procedure is described for the preparation of tri-O-acetyl-beta-L-fucopyranosylformaldoxime (1) involving stannate(II)-mediated reduction of the readily accessible tri-O-acetyl-beta-L-fucopyranosylnitromethane (3). The D-mannosyl, D-glucosyl, D-galactosyl, and D-xylosyl analogues 7-12 were prepared similarly. The structure of tetra-O-acetyl-beta-D-mannopyranosylformaldoxime (7) was determined by X-ray crystallography.

Original language	English
Pages (from-to)	1707-1715
Number of pages	9
Journal	Synthetic communications
Volume	33
Issue number	10
DOIs	https://doi.org/10.1081/SCC-120018932
Publication status	Published - 2003

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title = "A convenient synthesis of pyranosyl-1-carbaldoximes",

abstract = "A simple high-yielding procedure is described for the preparation of tri-O-acetyl-beta-L-fucopyranosylformaldoxime (1) involving stannate(II)-mediated reduction of the readily accessible tri-O-acetyl-beta-L-fucopyranosylnitromethane (3). The D-mannosyl, D-glucosyl, D-galactosyl, and D-xylosyl analogues 7-12 were prepared similarly. The structure of tetra-O-acetyl-beta-D-mannopyranosylformaldoxime (7) was determined by X-ray crystallography.",

author = "Baker, {K W J} and A Gibb and March, {A R} and S Parsons and Paton, {R M}",

year = "2003",

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language = "English",

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AU - Baker, K W J

AU - Gibb, A

AU - March, A R

AU - Parsons, S

AU - Paton, R M

PY - 2003

Y1 - 2003

N2 - A simple high-yielding procedure is described for the preparation of tri-O-acetyl-beta-L-fucopyranosylformaldoxime (1) involving stannate(II)-mediated reduction of the readily accessible tri-O-acetyl-beta-L-fucopyranosylnitromethane (3). The D-mannosyl, D-glucosyl, D-galactosyl, and D-xylosyl analogues 7-12 were prepared similarly. The structure of tetra-O-acetyl-beta-D-mannopyranosylformaldoxime (7) was determined by X-ray crystallography.

AB - A simple high-yielding procedure is described for the preparation of tri-O-acetyl-beta-L-fucopyranosylformaldoxime (1) involving stannate(II)-mediated reduction of the readily accessible tri-O-acetyl-beta-L-fucopyranosylnitromethane (3). The D-mannosyl, D-glucosyl, D-galactosyl, and D-xylosyl analogues 7-12 were prepared similarly. The structure of tetra-O-acetyl-beta-D-mannopyranosylformaldoxime (7) was determined by X-ray crystallography.

U2 - 10.1081/SCC-120018932

DO - 10.1081/SCC-120018932

M3 - Article

SN - 0039-7911

VL - 33

SP - 1707

EP - 1715

JO - Synthetic communications

JF - Synthetic communications

IS - 10

ER -

A convenient synthesis of pyranosyl-1-carbaldoximes

Abstract

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