Photoreaction of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-d-erythro-hex-2-enopyranoside with 1,3-dioxolane and tetrahydrofuran
✍ Scribed by Tohru Sakakibara; Toshio Nakagawa
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- English
- Weight
- 499 KB
- Volume
- 163
- Category
- Article
- ISSN
- 0008-6215
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📜 SIMILAR VOLUMES
## 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
## Abstract Die Methyl‐4,6‐__O__‐benzyliden‐2,3‐di‐__O__‐methylhexopyranoside mit D‐__gluco__‐ (**1**), D‐__altro__‐ (**3**) und D‐__allo__‐Konfiguration (**4**) reagieren mit n‐Butyllithium unter Methanol‐Eliminierung zu Methyl‐4,6‐__O__‐benzyliden‐3‐desoxy‐2‐__O__‐methyl‐α‐D‐__erythro__‐hex‐2‐eno
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