Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring

Jakob Fjord Tolborg; Knud Jørgen Jensen

doi:10.1039/a908446k

Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring

Jakob Fjord Tolborg, Knud Jørgen Jensen

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A tris(alkoxy)benzylamine (BAL) handle strategy was developed for safety-catch anchoring of D-glucosamine derivatives in solid-phase synthesis of oligosaccharides; the linkage between the BAL handle and the amine proved stable to conc. TFA and Lewis acids, but after N-acylation the amide could be released by treatment with TFA-H2O (19 : 1).

Original language	English
Journal	Chemical Communications
Issue number	2
Pages (from-to)	147-148
ISSN	1359-7345
DOIs	https://doi.org/10.1039/a908446k
Publication status	Published - 2000

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title = "Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring",

abstract = "A tris(alkoxy)benzylamine (BAL) handle strategy was developed for safety-catch anchoring of D-glucosamine derivatives in solid-phase synthesis of oligosaccharides; the linkage between the BAL handle and the amine proved stable to conc. TFA and Lewis acids, but after N-acylation the amide could be released by treatment with TFA-H2O (19 : 1). ",

author = "Tolborg, {Jakob Fjord} and Jensen, {Knud J{\o}rgen}",

year = "2000",

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journal = "Chemical Communications",

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AU - Tolborg, Jakob Fjord

AU - Jensen, Knud Jørgen

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N2 - A tris(alkoxy)benzylamine (BAL) handle strategy was developed for safety-catch anchoring of D-glucosamine derivatives in solid-phase synthesis of oligosaccharides; the linkage between the BAL handle and the amine proved stable to conc. TFA and Lewis acids, but after N-acylation the amide could be released by treatment with TFA-H2O (19 : 1).

AB - A tris(alkoxy)benzylamine (BAL) handle strategy was developed for safety-catch anchoring of D-glucosamine derivatives in solid-phase synthesis of oligosaccharides; the linkage between the BAL handle and the amine proved stable to conc. TFA and Lewis acids, but after N-acylation the amide could be released by treatment with TFA-H2O (19 : 1).

U2 - 10.1039/a908446k

DO - 10.1039/a908446k

M3 - Journal article

SN - 1359-7345

SP - 147

EP - 148

JO - Chemical Communications

JF - Chemical Communications

IS - 2

ER -

Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring

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