Facile Synthesis of 1,2-Anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone

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Title:Facile Synthesis of 1,2-Anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone
Creators:
Vukojevic, Nada
Dramicanin, Tatjana
Peric, Biljana
Popsavin, Mirjana
Csanádi, János
Miljković, Dušan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 7, pp. 1056-1059
Uncontrolled Keywords:1,2-Anhydro-5-<i>O</i>-tosyl-β-D-mannofuranurono-6,3-lactone, Uronolactones, 1,2-Anhydrosugars, D-Glucofuranurono-6,3-lactone, Carbohydrates

Abstract

A two-step synthesis of 1,2-anhydro-5-<i>O</i>-tosyl-β-D-mannofuranurono-6,3-lactone (<strong>1</strong>) has been achieved starting from D-glucofuranurono-6,3-lactone (<strong>2</strong>). Tosylation of <strong>2</strong> gave a mixture of 5-monotosylate <strong>3</strong> and 2,5-ditosylate <strong>4</strong> which were separated by crystallization followed by column chromatography. Acetylation of <strong>3</strong> gave 1,2-di-<i>O</i>-acetyl-5-<i>O</i>-tosyl-β-D-glucofuranurono-6,3-lactone (<strong>5</strong>) in the good yield. Treatment of ditosylate <strong>4</strong> with potassium carbonate in dry acetone afforded 1,2-anhydro-5-<i>O</i>-tosyl-β-D-mannofuranurono-6,3-lactone in 50% yield.

Title:Facile Synthesis of 1,2-Anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone
Creators:
Vukojevic, Nada
Dramicanin, Tatjana
Peric, Biljana
Popsavin, Mirjana
Csanádi, János
Miljković, Dušan
Uncontrolled Keywords:1,2-Anhydro-5-<i>O</i>-tosyl-β-D-mannofuranurono-6,3-lactone, Uronolactones, 1,2-Anhydrosugars, D-Glucofuranurono-6,3-lactone, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:7
Page Range:pp. 1056-1059
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19981056UNSPECIFIED
ID Code:1364
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:09

Citation

Vukojevic, Nada; Dramicanin, Tatjana; Peric, Biljana; Popsavin, Mirjana; Csanádi, János; Miljković, Dušan (1998) Facile Synthesis of 1,2-Anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone. Collection of Czechoslovak Chemical Communications, 63 (7). pp. 1056-1059. ISSN 0010-0765

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