Potential hexokinase inhibitors. Synthesis and properties of 2,3-anhydro-D-allose, 2,3-anhydro-D-ribose, and 2-O-methylsulphonyl-D-mannose

J. Grant Buchanan, David M Clode, Nadaraja Vethaviyasar

Research output: Contribution to journalArticle

Abstract

Hydrogenolysis of benzyl 2,3-anhydro-a-D-allopyranoside (4) in tetrahydrofuran over palladium-charcoal afforded crystalline 2,3-anhydro-a-D-allopyranose (6a). When dissolved in water this sugar underwent rapid mutarotation to give an equilibrium mixture containing mainly the a-pyranose (6a) (41%) and the ß-furanose (6d) (42%), together with the ß-pyranose (6b) and the a-furanose (6c) (5 and 12%, not individually assigned). 2,3-Anhydro-D-ribose, as an equilibrium mixture (13), has been prepared by hydrogenolysis of benzyl 2,3-anhydro-a-D- ribopyranoside (12). 2-O-Methylsulphonyl-a-D-mannopyranose (18) has been prepared and shown to give 1,6-anhydro-ß-D-glucopyranose (20) with base.

Original languageEnglish
Pages (from-to)1449-1453
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number13
Publication statusPublished - 1976

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Hydrogenolysis
Hexokinase
Ribose
Mannose
Charcoal
Palladium
Sugars
Crystalline materials
Water
2,3-anhydro-D-allose
tetrahydrofuran

Cite this

@article{68a8653c862749d8b3afe8924f804ffb,
title = "Potential hexokinase inhibitors. Synthesis and properties of 2,3-anhydro-D-allose, 2,3-anhydro-D-ribose, and 2-O-methylsulphonyl-D-mannose",
abstract = "Hydrogenolysis of benzyl 2,3-anhydro-a-D-allopyranoside (4) in tetrahydrofuran over palladium-charcoal afforded crystalline 2,3-anhydro-a-D-allopyranose (6a). When dissolved in water this sugar underwent rapid mutarotation to give an equilibrium mixture containing mainly the a-pyranose (6a) (41{\%}) and the {\ss}-furanose (6d) (42{\%}), together with the {\ss}-pyranose (6b) and the a-furanose (6c) (5 and 12{\%}, not individually assigned). 2,3-Anhydro-D-ribose, as an equilibrium mixture (13), has been prepared by hydrogenolysis of benzyl 2,3-anhydro-a-D- ribopyranoside (12). 2-O-Methylsulphonyl-a-D-mannopyranose (18) has been prepared and shown to give 1,6-anhydro-{\ss}-D-glucopyranose (20) with base.",
author = "Buchanan, {J. Grant} and Clode, {David M} and Nadaraja Vethaviyasar",
year = "1976",
language = "English",
pages = "1449--1453",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
number = "13",

}

Potential hexokinase inhibitors. Synthesis and properties of 2,3-anhydro-D-allose, 2,3-anhydro-D-ribose, and 2-O-methylsulphonyl-D-mannose. / Buchanan, J. Grant; Clode, David M; Vethaviyasar, Nadaraja.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 13, 1976, p. 1449-1453.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Potential hexokinase inhibitors. Synthesis and properties of 2,3-anhydro-D-allose, 2,3-anhydro-D-ribose, and 2-O-methylsulphonyl-D-mannose

AU - Buchanan, J. Grant

AU - Clode, David M

AU - Vethaviyasar, Nadaraja

PY - 1976

Y1 - 1976

N2 - Hydrogenolysis of benzyl 2,3-anhydro-a-D-allopyranoside (4) in tetrahydrofuran over palladium-charcoal afforded crystalline 2,3-anhydro-a-D-allopyranose (6a). When dissolved in water this sugar underwent rapid mutarotation to give an equilibrium mixture containing mainly the a-pyranose (6a) (41%) and the ß-furanose (6d) (42%), together with the ß-pyranose (6b) and the a-furanose (6c) (5 and 12%, not individually assigned). 2,3-Anhydro-D-ribose, as an equilibrium mixture (13), has been prepared by hydrogenolysis of benzyl 2,3-anhydro-a-D- ribopyranoside (12). 2-O-Methylsulphonyl-a-D-mannopyranose (18) has been prepared and shown to give 1,6-anhydro-ß-D-glucopyranose (20) with base.

AB - Hydrogenolysis of benzyl 2,3-anhydro-a-D-allopyranoside (4) in tetrahydrofuran over palladium-charcoal afforded crystalline 2,3-anhydro-a-D-allopyranose (6a). When dissolved in water this sugar underwent rapid mutarotation to give an equilibrium mixture containing mainly the a-pyranose (6a) (41%) and the ß-furanose (6d) (42%), together with the ß-pyranose (6b) and the a-furanose (6c) (5 and 12%, not individually assigned). 2,3-Anhydro-D-ribose, as an equilibrium mixture (13), has been prepared by hydrogenolysis of benzyl 2,3-anhydro-a-D- ribopyranoside (12). 2-O-Methylsulphonyl-a-D-mannopyranose (18) has been prepared and shown to give 1,6-anhydro-ß-D-glucopyranose (20) with base.

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