A practical route toward the preparation of 4,5:7,8‐di‐O‐isopropylidene KDO ethyl ester

G. J.P.H. Boons; P. A.M. van der Klein; G. A. van der Marel; J. H. van Boom

doi:10.1002/recl.19901090403

A practical route toward the preparation of 4,5:7,8‐di‐O‐isopropylidene KDO ethyl ester

G. J.P.H. Boons^*
, P. A.M. van der Klein
, G. A. van der Marel
, J. H. van Boom

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Condensation of 2,3: 5,6‐di‐O‐isopropylidene‐D‐mannopyranose with (ethoxycarbonylmethylene)triphenylphosphorane afforded the expected Wittig product. Reaction of the latter with chlorotrimethylsilane followed by methyl methanethiosulfate, in the presence of I. DA and after removal of the trimethylsilyl and unmasking of the dimethyl thioketal function, gave the title compound in a good overall yield.

Original language	English
Pages (from-to)	273-276
Number of pages	4
Journal	Recueil des Travaux Chimiques des Pays‐Bas
Volume	109
Issue number	4
DOIs	https://doi.org/10.1002/recl.19901090403
Publication status	Published - 1 Jan 1990
Externally published	Yes

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title = "A practical route toward the preparation of 4,5:7,8‐di‐O‐isopropylidene KDO ethyl ester",

abstract = "Condensation of 2,3: 5,6‐di‐O‐isopropylidene‐D‐mannopyranose with (ethoxycarbonylmethylene)triphenylphosphorane afforded the expected Wittig product. Reaction of the latter with chlorotrimethylsilane followed by methyl methanethiosulfate, in the presence of I. DA and after removal of the trimethylsilyl and unmasking of the dimethyl thioketal function, gave the title compound in a good overall yield.",

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doi = "10.1002/recl.19901090403",

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T1 - A practical route toward the preparation of 4,5:7,8‐di‐O‐isopropylidene KDO ethyl ester

AU - Boons, G. J.P.H.

AU - van der Klein, P. A.M.

AU - van der Marel, G. A.

AU - van Boom, J. H.

PY - 1990/1/1

Y1 - 1990/1/1

N2 - Condensation of 2,3: 5,6‐di‐O‐isopropylidene‐D‐mannopyranose with (ethoxycarbonylmethylene)triphenylphosphorane afforded the expected Wittig product. Reaction of the latter with chlorotrimethylsilane followed by methyl methanethiosulfate, in the presence of I. DA and after removal of the trimethylsilyl and unmasking of the dimethyl thioketal function, gave the title compound in a good overall yield.

AB - Condensation of 2,3: 5,6‐di‐O‐isopropylidene‐D‐mannopyranose with (ethoxycarbonylmethylene)triphenylphosphorane afforded the expected Wittig product. Reaction of the latter with chlorotrimethylsilane followed by methyl methanethiosulfate, in the presence of I. DA and after removal of the trimethylsilyl and unmasking of the dimethyl thioketal function, gave the title compound in a good overall yield.

UR - https://www.scopus.com/pages/publications/84987100707

U2 - 10.1002/recl.19901090403

DO - 10.1002/recl.19901090403

M3 - Article

AN - SCOPUS:84987100707

SN - 0165-0513

VL - 109

SP - 273

EP - 276

JO - Recueil des Travaux Chimiques des Pays‐Bas

JF - Recueil des Travaux Chimiques des Pays‐Bas

IS - 4

ER -

A practical route toward the preparation of 4,5:7,8‐di‐O‐isopropylidene KDO ethyl ester

Abstract

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