The allylation of dibutylstannylene derivatives of myo-inositol

✍ Scribed by Trupti Desai; Jill Gigg; Roy Gigg; Sheila Payne; Soledad Penades; Henry J. Rogers

• Publisher: Elsevier Science
• Year: 1992
• Tongue: English
• Weight: 1017 KB
• Volume: 216
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(92)84162-l

✦ Synopsis

Reaction of m.ro-inositol or a mixture of racemic 1,4-, 1.6-, and 4,5-di-O-allyl-mro-inositol in acetonitrile with dibutyltin oxide and ally1 bromide in the presence of tetrabutylammonium bromide gave, as the major products, a readily separable mixture of 1,3,4,6-and 1,3,4,5-tetra-O-allyl-~l~~~-inositol together with small proportions of penta-C-allyl-mr+inositols and 1,3,5-tri-O-allyl-rn~~~-inositol (from m_ro-inositol). Parallel results were obtained when crotyl bromide was used. When 3 equiv. ofdibutyltin oxide were used with m_r+inositol or 1 equiv. with the mixture of di-O-ally1 derivatives, 1,3,4-tri-O-allyl-m_ro-inosrtol was the major product. When 2 equiv. ofdibutyltin oxide were used. myo-inositol gave a complex mixture of mono-. di-, and tri-O-ally1 derivatives which was fractionated after conversion into the O-isopropylidene derivatives. Racemic 1,3,4,5-tetra-0-allyl-tityo-inositol was resolved via the (-)-w-camphanates, * Dedicated to Professor Grant Buchanan on the occasion of his 65th birthday. ' The Ally1 Group for Protection in Carbohydrate Chemistry. Part 23.