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Chapter 6,286

Regioselective oxidation of carbohydrate triols facile synthesis of 2 3 o isopropylidene beta d threohexo 2 4 diulopyranose and 1 2 o isopropylidene beta d threohexo 2 5 diulopyranose

Den Drijver, L.; Holzapfel, C.W.; Koekemoer, J.M.; Kruger, G.J.; Van Dyk, M.S.

Carbohydrate Research 155: 141-150

1986

ISSN/ISBN: 0008-6215
Accession: 006285141
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Stannylation of 2,3-O-isopropylidene-.beta.-D-fructopyranose with dibutylin oxide followed by brominolysis afforded 2,3-O-isopropylidene-.beta.-D-threo-hexo-2,4-diulopyranose, which was characterized as its oxime. Brominolysis of the O-dibutylstannylene derivative of 1,2-O-isopropylidene-.beta.-D-fructopyranose furnished 1,2-O-isopropylidene-.beta.-D-threo-hexo-2,5-diulopyranose, which was characterized as the corresponding O-methyloxime diacetate.

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Related References

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