Iodine:: A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides

K.P.R. Kartha; M. Aloui; R.A. Field

doi:10.1016/0040-4039(96)01029-5

Iodine: A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides

K.P.R. Kartha, M. Aloui, R.A. Field

Manchester Institute of Biotechnology

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

Abstract

Iodine has been found to be an efficient promoter in the alcoholysis of unprotected or fully benzylated methyl 1-thio-β-D-galactopyranoside. Stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis using “armed” thiomethyl glycosides as glycosyl donors was also observed. Protecting groups such as acetate, benzoate, benzylidene, isopropylidene, trimethylsilylethyl etc are stable under the reaction conditions.
Iodine has been found to be an efficient chemospecific activator of thiomethylglycosides in the stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis.

Original language	Undefined
Pages (from-to)	5175-5178
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	29
DOIs	https://doi.org/10.1016/0040-4039(96)01029-5
Publication status	Published - 1996

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Manchester Institute of Biotechnology

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10.1016/0040-4039(96)01029-5

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title = "Iodine:: A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides",

abstract = "Iodine has been found to be an efficient promoter in the alcoholysis of unprotected or fully benzylated methyl 1-thio-β-D-galactopyranoside. Stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis using “armed” thiomethyl glycosides as glycosyl donors was also observed. Protecting groups such as acetate, benzoate, benzylidene, isopropylidene, trimethylsilylethyl etc are stable under the reaction conditions.Iodine has been found to be an efficient chemospecific activator of thiomethylglycosides in the stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis.",

author = "K.P.R. Kartha and M. Aloui and R.A. Field",

year = "1996",

doi = "10.1016/0040-4039(96)01029-5",

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T2 - A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides

AU - Kartha, K.P.R.

AU - Aloui, M.

AU - Field, R.A.

PY - 1996

Y1 - 1996

N2 - Iodine has been found to be an efficient promoter in the alcoholysis of unprotected or fully benzylated methyl 1-thio-β-D-galactopyranoside. Stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis using “armed” thiomethyl glycosides as glycosyl donors was also observed. Protecting groups such as acetate, benzoate, benzylidene, isopropylidene, trimethylsilylethyl etc are stable under the reaction conditions.Iodine has been found to be an efficient chemospecific activator of thiomethylglycosides in the stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis.

AB - Iodine has been found to be an efficient promoter in the alcoholysis of unprotected or fully benzylated methyl 1-thio-β-D-galactopyranoside. Stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis using “armed” thiomethyl glycosides as glycosyl donors was also observed. Protecting groups such as acetate, benzoate, benzylidene, isopropylidene, trimethylsilylethyl etc are stable under the reaction conditions.Iodine has been found to be an efficient chemospecific activator of thiomethylglycosides in the stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis.

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U2 - 10.1016/0040-4039(96)01029-5

DO - 10.1016/0040-4039(96)01029-5

M3 - Article

SN - 0040-4039

VL - 37

SP - 5175

EP - 5178

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Iodine: A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides

Abstract

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