Synthesis of 2-deoxy, 3-deoxy, and 2,3-dideoxy analogs of α,α-trehalose by reductive desulfonyloxylation of p-toluenesulfonates with lithium triethylborohydride
作者:Hans H. Baer、Miroslawa Mekarska、Francine Boucher
DOI:10.1016/0008-6215(85)85207-1
日期:1985.2
Abstract Lithium triethylborohydride reacts readily with the 2-tosylate, the 2,2′-ditosylate, the 2,3,2′-tritosylate, and the 2,3,2′,3′-tetratosylate of 4,6;4′,6′-di-O-benzylidene-α,α-trehalose (1), to give products resulting both from O-desulfonylation and from reductive C-desulfonyloxylation. Among the products obtained were the known, symmetrically modified, 2,2′- and 3,3′-dideoxytrehalose analogs
摘要
三乙基硼氢化锂与4,6; 4'的2-
甲苯磺酸酯,
2,2'-二
甲苯磺酸酯,2,3,2'-三
甲苯磺酸酯和2,3,2',3'-四
甲苯磺酸酯容易发生反应, 6′-二-O-亚
苄基-α,α-
海藻糖(1),得到由O-去磺酰化和还原性C-去磺酰
氧基化产生的产物。在获得的产物中,是已知的对称修饰的具有α-d-
核糖,α-d-
核糖和α-d-
阿拉伯糖基的
2,2'-和3,3'-二
脱氧海藻
糖类似物(作为双亚
苄基乙缩醛),分别是α-d-
阿拉伯糖构型和三个新的晶体不对称类似物,即具有α-d -ribo的2,3'-二
脱氧异构体,α-d-
阿拉伯糖构型,2-单甲酰
氧基类似物(α-d-
核糖,α-d-
葡萄糖),和3-单甲酰
氧基类似物(α-d-
阿拉伯糖,α-d-
葡萄糖)。α-d -altro