Preparation of 2-Hydroxymethylated Aldose by the Stereospecific Rearrangement of Ketose
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- Ryoji Yanagihara
- Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223
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- Jun Egashira
- Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223
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- Sadao Yoshikawa
- Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223
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- Shuichi Osanai
- Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223
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Abstract
<jats:title>Abstract</jats:title> <jats:p>A simple one-stage reaction system which yields 2-C hydroxymethylated aldopentose has been investigated. Four different 2-C branched aldopentoses (2-C hydroxymethylated d-arabinose, d-ribose (Hamamelose), l-lyxose, and d-xylose) were prepared from the corresponding ketoses (d-psicose, d-fructose, l-sorbose, and d-tagatose, respectively). These branched sugars were synthesized by a similar mechanism to the 2-C epimerization of aldose using a nickel complex. It was confirmed that the isomerization of ketose to the side-branched sugar proceeded in the ternary nickel complex through a sequence of stereospecific rearrangements in the sugar. The yields were dependent upon the structure of the substrate ketose and the nickel-ethylenediamine complex. N,N′-Dialkylated cyclohexanediamines were the most suitable ligands for preparing the 2-C hydroxymethylated branched chain sugar.</jats:p>
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 68 (1), 237-242, 1995-01-01
Oxford University Press (OUP)
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Details 詳細情報について
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- CRID
- 1360565169057594240
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- NII Article ID
- 10008884888
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- NII Book ID
- AA00580132
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- ISSN
- 13480634
- 00092673
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- Data Source
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- Crossref
- CiNii Articles