Electronic Factors in the <i>C</i>-Glycosidation with Silylacetylene

• Minoru Isobe

  Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya UniversityChikusa-Ku, Nagoya

• Rungnapha Saeeng

  Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya UniversityChikusa-Ku, Nagoya

• Rena Nishizawa

  Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya UniversityChikusa-Ku, Nagoya

• Masato Konobe

  Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya UniversityChikusa-Ku, Nagoya

• Toshio Nishikawa

  Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya UniversityChikusa-Ku, Nagoya

Abstract

Two kinds of electronic factors have been clarified to control the reactivity in alkynylation of glycals with silylacetylenes. One is that the reactivity of nucleophile silylpropargyl alcohol derivative largely depends on the protecting group. The second factor is found in the similar electrophiles as oxocarbenium intermediates that were generated from glucals or galactals. Diminished reactivity was found with the 4-axial substituents such as acetoxy or methoxy group.

Journal

• Chemistry Letters

  Chemistry Letters 28 (6), 467-468, 1999-06-01

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360565169063093888
• NII Article ID: 10004485962
• NII Book ID: AA00603318
• DOI: 10.1246/cl.1999.467
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/28/6/467/56076837/cl.1999.467.pdf
• Data Source:
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  • CiNii Articles