Reactions of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p- tolylsulfonyl-β-d-erythro-hex-2-enopyranoside and its phenyl analog with several nucleophiles; stereoselective preparation of 3-O-acyl-d-arabino- and d-ribo-hex-1-enitol derivatives
✍ Scribed by Izumi Takai; Azuma Yamamoto; Yoshiharu Ishido; Tohru Sakakibara; Emiko Yagi
- Book ID
- 107726032
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- English
- Weight
- 980 KB
- Volume
- 220
- Category
- Article
- ISSN
- 0008-6215
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## Nucleophilic addition-reactions of the title compound, prepared from the corresponding 3-nitrohex-2-enitol, were investigated under kinetically controlled conditions; such sterically bulky nucleophiles as tert-butyl peroxide and 2,4-pentanedionate ions (except in 1,Cdioxane) were found to enga
Reactions of the title compounds with sodium methoxide and sodium borodeuteride were found to proceed mainly via the SK2' mechanism; nucleophiles selectively attacked the anomeric carbon atom from the same side of the leaving acetoxyl group at C-3.
Reactions of the title compounds with several nucelophiles suggested that the ring oxygen atom (0-5) accelerated the reactivity of the nitro alkene moiety, but scarcely affected the stereoselectivity of the nucleophilic attack.
IZUMI TAKAI, YOSHIFUSA TACHIMORI, AZUMA YAMAMOTO, YOSHIHARU ISHIDO\*, AND (the late) ROKURO SUWH