4-Hydroxymethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole

Brendan Wilkinson; Laurent F Bornaghi; Todd A Houston; Sally-Ann Poulsen; Alan R White

doi:10.1107/s1600536806040864

4-Hydroxymethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole

Brendan Wilkinson
, Laurent F Bornaghi
, Todd A Houston
, Sally-Ann Poulsen
, Alan R White

Chemistry

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

5 Citations (Scopus)

Abstract

The structure of the title compound, C₁₇H₂₃N₃O₁₀, (2), has been determined as part of our investigation into the synthetic utility of the glucosyl triazole unit in carbohydrate chemistry. Compound (2) was synthesized by the 1,3-dipolar cycloaddition reaction of propargyl alcohol with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide under conditions which afforded (2) exclusively with complete retention of anomeric stereochemistry. The six-membered carbohydrate ring adopts a chair conformation. The non-H substituents are located in equatorial positions.

Original language	English
Pages (from-to)	o5065-o5067
Journal	Acta crystallographica. Section E
Volume	62
Issue number	11
DOIs	https://doi.org/10.1107/s1600536806040864
Publication status	Published - 2006

Keywords

Organic Chemical Synthesis
Instrumental Methods (excl. Immunological and Bioassay Methods)

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https://hdl.handle.net/1959.11/22905

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@article{01c35fe394054e9a8f9d2813887eb2fb,

title = "4-Hydroxymethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole",

abstract = "The structure of the title compound, C₁₇H₂₃N₃O₁₀, (2), has been determined as part of our investigation into the synthetic utility of the glucosyl triazole unit in carbohydrate chemistry. Compound (2) was synthesized by the 1,3-dipolar cycloaddition reaction of propargyl alcohol with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide under conditions which afforded (2) exclusively with complete retention of anomeric stereochemistry. The six-membered carbohydrate ring adopts a chair conformation. The non-H substituents are located in equatorial positions.",

keywords = "Organic Chemical Synthesis, Instrumental Methods (excl. Immunological and Bioassay Methods)",

author = "Brendan Wilkinson and Bornaghi, \{Laurent F\} and Houston, \{Todd A\} and Sally-Ann Poulsen and White, \{Alan R\}",

year = "2006",

doi = "10.1107/s1600536806040864",

language = "English",

volume = "62",

pages = "o5065--o5067",

journal = "Acta crystallographica. Section E",

issn = "1600-5368",

publisher = "International Union of Crystallography (IUCr)",

number = "11",

}

TY - JOUR

T1 - 4-Hydroxymethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole

AU - Wilkinson, Brendan

AU - Bornaghi, Laurent F

AU - Houston, Todd A

AU - Poulsen, Sally-Ann

AU - White, Alan R

PY - 2006

Y1 - 2006

N2 - The structure of the title compound, C₁₇H₂₃N₃O₁₀, (2), has been determined as part of our investigation into the synthetic utility of the glucosyl triazole unit in carbohydrate chemistry. Compound (2) was synthesized by the 1,3-dipolar cycloaddition reaction of propargyl alcohol with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide under conditions which afforded (2) exclusively with complete retention of anomeric stereochemistry. The six-membered carbohydrate ring adopts a chair conformation. The non-H substituents are located in equatorial positions.

AB - The structure of the title compound, C₁₇H₂₃N₃O₁₀, (2), has been determined as part of our investigation into the synthetic utility of the glucosyl triazole unit in carbohydrate chemistry. Compound (2) was synthesized by the 1,3-dipolar cycloaddition reaction of propargyl alcohol with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide under conditions which afforded (2) exclusively with complete retention of anomeric stereochemistry. The six-membered carbohydrate ring adopts a chair conformation. The non-H substituents are located in equatorial positions.

KW - Organic Chemical Synthesis

KW - Instrumental Methods (excl. Immunological and Bioassay Methods)

U2 - 10.1107/s1600536806040864

DO - 10.1107/s1600536806040864

M3 - Article

SN - 1600-5368

VL - 62

SP - o5065-o5067

JO - Acta crystallographica. Section E

JF - Acta crystallographica. Section E

IS - 11

ER -

4-Hydroxymethyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole

Abstract

Keywords

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