Thiol addition to protected allyl glycosides: An improved method for the preparation of spacer-arm glycosides

Paul B. Van Seeventer; Johannes A.L.M. Van Dorst; John F. Siemerink; Johannis P. Kamerling; Johannes F.G. Vliegenthart

doi:10.1016/S0008-6215(97)00074-8

Thiol addition to protected allyl glycosides: An improved method for the preparation of spacer-arm glycosides

Paul B. Van Seeventer, Johannes A.L.M. Van Dorst, John F. Siemerink, Johannis P. Kamerling, Johannes F.G. Vliegenthart

Bijvoet Center

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

Abstract

A useful method for the preparation of differently functionalized sulfide spacer-arm glycosides is presented. Several protected allyl glycosides were variously elongated via a radical addition reaction with pentanethiol, methyl 3-mercaptopropionate, or 2-mercaptoethanol. The hydroxyl function of protected 3-(2-hydroxyethylthio)propyl glycosides was subsequently transformed into an azide function.

Original language	English
Pages (from-to)	369-373
Number of pages	5
Journal	Carbohydrate Research
Volume	300
Issue number	4
DOIs	https://doi.org/10.1016/S0008-6215(97)00074-8
Publication status	Published - 19 May 1997

Keywords

glycoconjugate
glycoside
article
carbohydrate synthesis
chemical modification
chemical reaction
drug synthesis
priority journal

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10.1016/S0008-6215(97)00074-8

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@article{e8ad7527c32b42729d3207c54fc48682,

title = "Thiol addition to protected allyl glycosides: An improved method for the preparation of spacer-arm glycosides",

abstract = "A useful method for the preparation of differently functionalized sulfide spacer-arm glycosides is presented. Several protected allyl glycosides were variously elongated via a radical addition reaction with pentanethiol, methyl 3-mercaptopropionate, or 2-mercaptoethanol. The hydroxyl function of protected 3-(2-hydroxyethylthio)propyl glycosides was subsequently transformed into an azide function.",

keywords = "glycoconjugate, glycoside, article, carbohydrate synthesis, chemical modification, chemical reaction, drug synthesis, priority journal",

author = "{Van Seeventer}, {Paul B.} and {Van Dorst}, {Johannes A.L.M.} and Siemerink, {John F.} and Kamerling, {Johannis P.} and Vliegenthart, {Johannes F.G.}",

year = "1997",

month = may,

day = "19",

doi = "10.1016/S0008-6215(97)00074-8",

language = "English",

volume = "300",

pages = "369--373",

journal = "Carbohydrate Research",

issn = "0008-6215",

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TY - JOUR

T1 - Thiol addition to protected allyl glycosides: An improved method for the preparation of spacer-arm glycosides

AU - Van Seeventer, Paul B.

AU - Van Dorst, Johannes A.L.M.

AU - Siemerink, John F.

AU - Kamerling, Johannis P.

AU - Vliegenthart, Johannes F.G.

PY - 1997/5/19

Y1 - 1997/5/19

N2 - A useful method for the preparation of differently functionalized sulfide spacer-arm glycosides is presented. Several protected allyl glycosides were variously elongated via a radical addition reaction with pentanethiol, methyl 3-mercaptopropionate, or 2-mercaptoethanol. The hydroxyl function of protected 3-(2-hydroxyethylthio)propyl glycosides was subsequently transformed into an azide function.

AB - A useful method for the preparation of differently functionalized sulfide spacer-arm glycosides is presented. Several protected allyl glycosides were variously elongated via a radical addition reaction with pentanethiol, methyl 3-mercaptopropionate, or 2-mercaptoethanol. The hydroxyl function of protected 3-(2-hydroxyethylthio)propyl glycosides was subsequently transformed into an azide function.

KW - glycoconjugate

KW - glycoside

KW - article

KW - carbohydrate synthesis

KW - chemical modification

KW - chemical reaction

KW - drug synthesis

KW - priority journal

U2 - 10.1016/S0008-6215(97)00074-8

DO - 10.1016/S0008-6215(97)00074-8

M3 - Article

SN - 0008-6215

VL - 300

SP - 369

EP - 373

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 4

ER -

Thiol addition to protected allyl glycosides: An improved method for the preparation of spacer-arm glycosides

Abstract

Keywords

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