Synthesis of benzyl 2-azido-2-deoxy-4-O-β-d-glucopyranosyl-α-d-glucopyranoside and 1,6-anhydro-2-azido-2-deoxy-4-O-β-d-glucopyranosyl-β-d-glucopyranose

Tony Kung Ming Shing, Arthur S. Perlin

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The title compounds were prepared from cellobiose by means of two series of transformations. One series entailed the azidonitration of 3,6-di-O-acetyl-1,5-anhydro-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-d- glucopyranosyl)-d-arabino-hex-1-enitol to give 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(tetra-O-acetyl-β-d-glucopyranosyl)-β-d-glucopyranosyl nitrate, which was then converted into the benzyl α-glycoside. Minor by-products of the azidonitration reaction were also identified. For the second synthesis, 1,6-anhydro-β-cellobiose was converted into 1,6-anhydro-4-O-(4,6-O-isopropylidene-β-d-glucopyranosyl)- β-d-glucopyranose (15). The azido function was then introduced at the C-2 position of the 1,6-anhydro residue, by a displacement reaction involving the 2,3-anhydro-d-manno analog of 15 as an intermediate compound.

Original languageEnglish
Pages (from-to)65-72
Number of pages8
JournalCarbohydrate Research
Volume130
Issue numberC
DOIs
Publication statusPublished - 1984 Jul 15
Externally publishedYes

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Cellobiose
Glycosides
Nitrates
Byproducts
propylene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Synthesis of benzyl 2-azido-2-deoxy-4-O-β-d-glucopyranosyl-α-d-glucopyranoside and 1,6-anhydro-2-azido-2-deoxy-4-O-β-d-glucopyranosyl-β-d-glucopyranose. / Shing, Tony Kung Ming; Perlin, Arthur S.

In: Carbohydrate Research, Vol. 130, No. C, 15.07.1984, p. 65-72.

Research output: Contribution to journalArticle

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abstract = "The title compounds were prepared from cellobiose by means of two series of transformations. One series entailed the azidonitration of 3,6-di-O-acetyl-1,5-anhydro-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-d- glucopyranosyl)-d-arabino-hex-1-enitol to give 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(tetra-O-acetyl-β-d-glucopyranosyl)-β-d-glucopyranosyl nitrate, which was then converted into the benzyl α-glycoside. Minor by-products of the azidonitration reaction were also identified. For the second synthesis, 1,6-anhydro-β-cellobiose was converted into 1,6-anhydro-4-O-(4,6-O-isopropylidene-β-d-glucopyranosyl)- β-d-glucopyranose (15). The azido function was then introduced at the C-2 position of the 1,6-anhydro residue, by a displacement reaction involving the 2,3-anhydro-d-manno analog of 15 as an intermediate compound.",
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AB - The title compounds were prepared from cellobiose by means of two series of transformations. One series entailed the azidonitration of 3,6-di-O-acetyl-1,5-anhydro-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-d- glucopyranosyl)-d-arabino-hex-1-enitol to give 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(tetra-O-acetyl-β-d-glucopyranosyl)-β-d-glucopyranosyl nitrate, which was then converted into the benzyl α-glycoside. Minor by-products of the azidonitration reaction were also identified. For the second synthesis, 1,6-anhydro-β-cellobiose was converted into 1,6-anhydro-4-O-(4,6-O-isopropylidene-β-d-glucopyranosyl)- β-d-glucopyranose (15). The azido function was then introduced at the C-2 position of the 1,6-anhydro residue, by a displacement reaction involving the 2,3-anhydro-d-manno analog of 15 as an intermediate compound.

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