Abstract
Reaction of sugar allyl bromides with tri-n-butyltin cuprate gives sugar allyltin derivatives with retention of the configuration of the double bond, what enables to prepare pure trans or cis olefins. Sugar aldehydes of the general formula Sug-CHO react also with ‘Bu 3SnCu’ to give α-tri-n-butyltin carbinols SugCH(OH)-SnBu 3. Reaction of “Bu 3SnCu” with α,β-unsaturated sugar aldehydes resulted in 1,4-addition and afforded products of the general formula Sug-CH-SnBu 3 CH 2 CHO. Treatment of these compounds with zinc chloride affords open chain aldehydes with elimination of the tri-n-butyltin moiety.
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