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化学学报
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化学学报 ›› 1957, Vol. 23 ›› Issue (1): 68-75. 上一篇    下一篇

论文

内醚糖的研究Ⅳ.2,3-内醚-5-去羟-α-和β-D-来苏糖甲基甙

张滂1, 刘育亭2   

  1. 1. 北京大学化学系;
    2. 北京大学化学系
  • 投稿日期:1956-11-10 发布日期:2013-06-03

ANHYDRO SUGARS. PART Ⅳ. METHYL 2, 3-ANHYDRO-α-AND-β-D-LYXOMETHYLOSIDE

CHAHG PANG1, LIU YUOH-TING2   

  1. Department of Chemistry, Peking University
  • Received:1956-11-10 Published:2013-06-03

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自2,3-内醚-α-和β-D-来苏糖甲基呋喃甙(Ⅳ,α和β)合成了2,3-内醚5-去羟-α-和β-D-来苏糖甲基甙(Ⅶ,α和β).合成的步骤为:2,3-内醚-α-和β-D-来苏糖甲基呋喃甙(Ⅳ,α和β)→2,3-内醚-5-O-对甲苯矿酰基-α-和β-D-来苏糖甲基呋喃甙(V,α和β)→2,3-内醚-5-碘代-5-去羟-α-和β-D-来苏糖甲基甙(Ⅵ,α和β)→2,3-内醚-5-去羟-α-和β-D-来苏糖甲基甙(Ⅶ,α和β).除了最后一对外,其余的中间物都是结晶的.本工作得到了结晶的2-O-对甲苯矿酰基-3,5-异丙亚基-α-和β-D-木糖甲基呋喃甙(Ⅱ,α和β).水解后,α-端基差向异构体生成美丽的2-O-对甲苯矿酰基-α-D-木糖甲基呋喃甙(Ⅲα,R=Ts)晶体,可是在同样的处理下,β-端基差向异构体却只是糖浆状产物(Ⅲβ,R=Ts).

The title compounds were synthesized respectively from methyl 2,3-anhydro-α- and β-D-lyxofuranoside (Ⅳ,α and β).This consists of: Methyl 2,3-anhydro-α- and β-D-lyxofuranoside (Ⅳ,α and β)→methyl 2,3-anhydro-5-O-toluene-ρ-sulphonyl-α- and β-D-lyxofuranosid ( Ⅴ,α and β )→methyl 2,3-anhydro-5-iodo-5-deoxy-α-and β-D-lyxofuranoside (Ⅵ,α and β)→methyl 2,3-anhydro-α-and β-D-lyxomethyloside (Ⅶ,a and β).All the intermediates are crystalline except the last ones.