Branched-chain Sugars. XII. The Stereoselectivities in the Reaction of Methyl 4,6-O-Benzylidene-α- and -β-D-hexopyranosid-3-uloses with Diazomethane

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概要

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• The stereoselectivities in the diazomethane reaction of methyl 4,6-O-benzylidene-2-O-methyl-α-D-ribo-hexopyranosid-3-ulose (2), its 2-epimer (3), β-anomer of 2 and the corresponding 2-O-Benzoyl derivative were examined, in comparison with those in the Grignard reaction and sodium borohydride reduction. The complemental stereoselectivity of diazomethane reaction in the case of 2 and 3 indicated that the electrostatic attractive effect in the transition state between diazomethyl cation and the axial methoxyl oxygen at the α-position to carbonyl function in 3 is much stronger than that at β-position which is predominat in the case of 2. In cases of β-anomers having no axial oxygen, stereoselectivies were preferentially controlled by the usual steric factors.

• 日本化学会の論文

著者

• 佐藤 憲一

  Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University

• Sato Ken-ichi

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

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