Selective synthesis of 1,6-anhydro-β-d-mannopyranose and -mannofuranose using microwave-assisted heating

The dehydration of d-mannose and the demethanolization of methyl-α-d-mannopyranoside (MαMP) or methyl-α-d-mannofuranoside (MαMF) were examined using microwave-assisted heating for a 3-min irradiation at temperature from 120 to 280°C in ordinary or dry sulfolane without any catalyst. The microwave-as...

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Bibliographic Details
Published in:Carbohydrate research 2011-09, Vol.346 (13), p.1747-1751
Main Authors: Hoai, Nguyen To, Sasaki, Akiyoshi, Sasaki, Masahide, Kaga, Harumi, Kakuchi, Toyoji, Satoh, Toshifumi
Format: Article
Language:English
Subjects:
1,6-Anhydrosugar
Anhydromannose
catalysts
Chromatography, Gas
Demethanolization
heat
Heating
irradiation
mannose
Mannose - chemical synthesis
Mannose - chemistry
Methylmannofuranoside
Methylmannopyranoside
Methylmannosides - chemistry
Microwave
microwave treatment
Microwaves
temperature
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Summary:The dehydration of d-mannose and the demethanolization of methyl-α-d-mannopyranoside (MαMP) or methyl-α-d-mannofuranoside (MαMF) were examined using microwave-assisted heating for a 3-min irradiation at temperature from 120 to 280°C in ordinary or dry sulfolane without any catalyst. The microwave-assisted heating of MαMP and MαMF smoothly proceeded to selectively afford the anhydromannoses, 1,6-anhydro-β-d-mannopyranose (AMP) and 1,6-anhydro-β-d-mannofuranose (AMF), respectively, in high yields. For MαMP in ordinary sulfolane at 240°C, AMP was selectively obtained in the AMF:AMP ratio of 4:96, whereas AMF was the major product at the AMF:AMP ratio of 97:3 from MαMF in dry sulfolane at 220°C.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.05.032