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

K. P.Ravindranathan Kartha; Mahmoud Aloui; Robert 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.Ravindranathan Kartha, Mahmoud Aloui, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

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

52 Citations (Scopus)

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.

Original language	English
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 - 15 Jul 1996

Access to Document

10.1016/0040-4039(96)01029-5

Cite this

@article{e77c86ea1fb7423a91a9295beb1b49fa,

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.",

author = "Kartha, {K. P.Ravindranathan} and Mahmoud Aloui and Field, {Robert A.}",

year = "1996",

month = jul,

day = "15",

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

language = "English",

volume = "37",

pages = "5175--5178",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "29",

}

TY - JOUR

T1 - Iodine: A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides

AU - Kartha, K. P.Ravindranathan

AU - Aloui, Mahmoud

AU - Field, Robert A.

PY - 1996/7/15

Y1 - 1996/7/15

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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0030586210&partnerID=8YFLogxK

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

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

M3 - Article

AN - SCOPUS:0030586210

VL - 37

SP - 5175

EP - 5178

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 29

ER -

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

Abstract

Access to Document

Other files and links

Cite this