A one-step synthesis of azide-tagged carbohydrates

Versatile intermediates for glycotechnology

Aditya K. Sanki, Lara Mahal

Research output: Contribution to journalArticle

Abstract

Herein we describe a simple and practical methodology for accessing both the α-anomers (D-mannose, N-acetyl-D-glucosamine, N-acetyl-D- galactosamine, D-lactose) and α- and β-anomers (D-glucose, D-galactose, L-fucose) of 2′-azidoethyl and azidotriethylene glycol glycosides using free sugars and Dowex 50 (resin) as an efficient catalyst. These azidoalkyl glycosides are increasingly useful synthetic intermediates for glycotechnology.

Original languageEnglish (US)
Pages (from-to)455-459
Number of pages5
JournalSynlett
Issue number3
DOIs
StatePublished - Feb 15 2006

Fingerprint

Azides
Glycosides
Carbohydrates
Acetylgalactosamine
Glycols
Fucose
Acetylglucosamine
Lactose
Mannose
Galactose
Sugars
Resins
Catalysts
Dowex 50

Keywords

  • Azidoethyl glycosides
  • Azidotriethylene glycol glycosides
  • Glycotechnology
  • Resin-catalyzed glycosylation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A one-step synthesis of azide-tagged carbohydrates : Versatile intermediates for glycotechnology. / Sanki, Aditya K.; Mahal, Lara.

In: Synlett, No. 3, 15.02.2006, p. 455-459.

Research output: Contribution to journalArticle

@article{4952826432324633aadbecdf9b9cdc83,
title = "A one-step synthesis of azide-tagged carbohydrates: Versatile intermediates for glycotechnology",
abstract = "Herein we describe a simple and practical methodology for accessing both the α-anomers (D-mannose, N-acetyl-D-glucosamine, N-acetyl-D- galactosamine, D-lactose) and α- and β-anomers (D-glucose, D-galactose, L-fucose) of 2′-azidoethyl and azidotriethylene glycol glycosides using free sugars and Dowex 50 (resin) as an efficient catalyst. These azidoalkyl glycosides are increasingly useful synthetic intermediates for glycotechnology.",
keywords = "Azidoethyl glycosides, Azidotriethylene glycol glycosides, Glycotechnology, Resin-catalyzed glycosylation",
author = "Sanki, {Aditya K.} and Lara Mahal",
year = "2006",
month = "2",
day = "15",
doi = "10.1055/s-2006-926264",
language = "English (US)",
pages = "455--459",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "3",

}

TY - JOUR

T1 - A one-step synthesis of azide-tagged carbohydrates

T2 - Versatile intermediates for glycotechnology

AU - Sanki, Aditya K.

AU - Mahal, Lara

PY - 2006/2/15

Y1 - 2006/2/15

N2 - Herein we describe a simple and practical methodology for accessing both the α-anomers (D-mannose, N-acetyl-D-glucosamine, N-acetyl-D- galactosamine, D-lactose) and α- and β-anomers (D-glucose, D-galactose, L-fucose) of 2′-azidoethyl and azidotriethylene glycol glycosides using free sugars and Dowex 50 (resin) as an efficient catalyst. These azidoalkyl glycosides are increasingly useful synthetic intermediates for glycotechnology.

AB - Herein we describe a simple and practical methodology for accessing both the α-anomers (D-mannose, N-acetyl-D-glucosamine, N-acetyl-D- galactosamine, D-lactose) and α- and β-anomers (D-glucose, D-galactose, L-fucose) of 2′-azidoethyl and azidotriethylene glycol glycosides using free sugars and Dowex 50 (resin) as an efficient catalyst. These azidoalkyl glycosides are increasingly useful synthetic intermediates for glycotechnology.

KW - Azidoethyl glycosides

KW - Azidotriethylene glycol glycosides

KW - Glycotechnology

KW - Resin-catalyzed glycosylation

UR - http://www.scopus.com/inward/record.url?scp=33344465143&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33344465143&partnerID=8YFLogxK

U2 - 10.1055/s-2006-926264

DO - 10.1055/s-2006-926264

M3 - Article

SP - 455

EP - 459

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 3

ER -