Orientation of the Addition of Dimethyl Phosphonate to 5,6-Dideoxy-6-nitro-D-hex-5-enofuranoses

DOI: 10.1246/bcsj.65.1154

Source and publish data:

Bulletin of the Chemical Society of Japan p. 1154 - 1156 (1992)

Update date:2022-08-03

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Authors:

Hanaya, Tadashi

Yamamoto, Hiroshi

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Article abstract of DOI:10.1246/bcsj.65.1154

The addition of dimethyl phosphonate to six 5,6-dideoxy-6-nitro-D-hex-5-enofuranoses at 25 deg C in the presence of triethylamine preponderantly gave (5R)-adducts, whereas the same reaction at 100 deg C without a base yielded (5S)-adducts as the main products.

Full text of DOI:10.1246/bcsj.65.1154

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Product name:[(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester

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