三种脱氧核苷5′-O-对甲苯磺酸酯的合成

SYNTHESIS OF 5′ TOSYL DERIVATIVES OF 2′,3′ DIDEOXY NUCLEOSIDES

首次合成了５′－Ｏ－对甲苯磺酰基－２′，３′－二脱氢－２′，３′－二脱氧腺苷（５′－ＴｓＯ－Ｄ４Ａ）、５′－Ｏ－对甲苯磺酰基－２′，３′－二脱氧尿苷（５′－ＴｓＯ－Ｄ４Ｕ）、５′－Ｏ－对甲苯磺酰基－２′，３′－二脱氧尿苷（５′－ＴｓＯ－ＤＤＵ）等三个对甲苯磺酰化的脱氧核苷修饰物，并通过１ＨＮＭＲ、ＵＶ／Ｖｉｓ、ＭＳ等方法进行了表征．对脱氧核苷及其５′修饰物二维ＣＯＳＹ谱的测定为糖环上各类氢原子正确归属提供了依据．

A novel 5′ O p tolylsulfonyl 2′,3 didehydro 2′,3′ dideoxyadensine(TsO D 4A) and other analogues of 2′,3′ didehydro 2′,3′ dideoxyuridine (RsO D 4U) and 2′,3′ dideoxyuridine (TsO DDU)( A=adenosine, U=uridine)were synthesized by tosylation of the 2′,3′ dideoxynucleoside or 2′,3′ unsaturated dideoxynucleoside. They are characterized by UV/vis, 1H NMR and MS. The chemical shifts for dideoxynucleosides and their 5′ tosyl derivatives were assigned through 2D 1H 1H COSY from which the exact positions for 2′ H and 3′ H were given.