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Communication | Regular issue | Vol 38, No. 7, 1994, pp.1449-1452
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6665
Novel Efficient Synthesis and Structural Analysis of Furanose-Type Phosphono Sugars

Mitsuji Yamashita,* Akihiro Yabui, Tatsuo Oshikawa, Tadashi Hanaya, and Hiroshi Yamamoto

*Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan

Abstract

Reaction of 2-benzyloxymethyl-1-methoxy-3-phospholene 1-oxide with mCPBA afforded 3,4-epoxyphospholane derivatives, whose isomerized allylic alcohols were cis-dihydroxylated by osmium(VIII) oxide-catalyzed oxidation to give ribo-, arabino-, xylo-, and lyxo-furanose-type phosphono sugars. The nmr data suggest a twist conformation.