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Organoaluminium induced ring-opening of epoxypyranosides. IV. Synthesis and structure of γ- hydroxy-lsoleucine stereoisomers and their corresponding lactones.

✍ Scribed by Tord Inghardt; Torbjörn Frejd; Göran Svensson


Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
919 KB
Volume
47
Category
Article
ISSN
0040-4020

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✦ Synopsis


Key Wordy: tnmethylaluminium; opening of epoxide and pymnoside rings; 2.3~anhydr+L-ribopyranosik y-hydroxy-i&wine;

x-ray data.

Abstmct: Two r hydroxy-isoleucine stereoisomers 8 (2R. 3R, 4R), and 14 (2s. 3R, 4R) as well as their corresponding y lactones 9 and IS were synthesised using a tandem, Me3Al induced open& of the epoxide and pyranoside rings of benzyl23-anhydro4-O-(terr-buyldmze~hylsilyl)-~L-ribopyranos& (I). The structure of the iactone hydrochloride 9

was confirmed by an X-ray crystal structure determutation.