APPLICATION OF TRI-N-BUTYLTIN CUPRATE IN SUGAR CHEMISTRY

Reaction of sugar allyl bromides with tri-n-butyltin cuprate gives sug ar allyltin derivatives with retention of the configuration of the dou ble bond, what enables to prepare pure trans or cis olefins. Sugar ald ehydes of the general formula Sug-CHO react also with 'Bu(3)SnCu' to g ive alpha-tri-n-butyltin carbinols SugCH(OH)-SnBu(3). Reaction of ''Bu (3)SnCu'' with alpha,beta-unsaturated sugar aldehydes resulted in 1,4- addition and afforded products of the general formula Sug-CH-SnBu(3) - CH2 CHO. Treatment of these compounds with zinc chloride affords open chain aldehydes with elimination of the tri-n-butyltin moiety. (C) 199 6 Elsevier Science Ltd.