Abstract
Alkylmagnesium chlorides react with methyl 2,3-anhydro-4,6- O-benzylidene-α- d-mannopyranoside ( 1) and -α- d-allopyranoside ( 2) to give, preponderantly, 3-alkyl and 2-alkyl, branched-chain, deoxy sugars. In contrast, alkylmagnesium iodides and bromides do not give branched-chain, deoxy sugars with 1 and 2 but give, initially, halohydrins which undergo elimination and reduction with excess of Grignard reagent. Preliminary investigations of the reaction of 2 with a complex derived from alkyl-magnesium iodides and tetrahydropyran indicate the formation of methyl 4,6- o-benzylidene-3-deoxy-3-iodo-α- d-glucopyranoside ( 13b) by trans-diequatorial opening of epoxide 2, whereas normal Grignard reagents (alkylmagnesium iodides) react with 2 in tetrahydropyran to give the usual trans-diaxial product ( 14b).
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