高等学校化学学报 ›› 1985, Vol. 6 ›› Issue (3): 225.

• 研究论文 • 上一篇    下一篇

2-O-苄基-3,5-内醚-α和β-D-木呋喃甲基甙的合成

曹玲华, 刘育亭   

  1. 新疆大学化学系
  • 收稿日期:1983-05-07 出版日期:1985-03-24 发布日期:1985-03-24

Synthesis of Methyl 2-O-Benzyl-3,5-Anhydro-α-and β-D-Xylofuranoside

Cao Lingbua, Liu Yuting   

  1. Department of Chemistry, Xinjiang University, Wulumuqi
  • Received:1983-05-07 Online:1985-03-24 Published:1985-03-24

摘要: 本文报导一对具有2,6-二氧杂双环[3.2.0]庚烷骨架的四元环内醚型戊糖甙差向异构体的合成.其关键化合物2-O-苯甲基-3,5-二-O-对甲苯磺酰基-α-和β-D-木呋喃甲基甙(S)、2-O-苯甲基-5-O-对甲苯磺酰基-α-D-木呋喃甲基甙及其3-O-乙酰基衍生物均以结晶形固体制得,由这些结晶分别制得标题化合物.

Abstract: The title compounds with the 2, 6-dioxabicyclo-[3.2.0]-heptane skeleton were synthesized respectively from methyl 3,5-O-(1-methylethylidene)-α- and β-D-xylofuranoside (IAand IB) in five steps. This consists of benzylation, deacetonation, tosylation, acetylation and ring closure. Then the eight intermediates i.e. methyl 2-O-benzyl-3,5-O-(1-methylethylidene)-α- and β-D-xylofuranoside (ⅡA, ⅡB), methyl 2-O-benzyl-α- and β-D-xylofuranoside (ⅢA, ⅢB), methyl 2-O-benzyl-3, 5-di-O-tosyl-β-D-xylofuranoside (ⅣB), methyl 2-O-benzyl-3-O-acetyl-5-O-tosyl-a-D-xylofuranoside (Ⅵ A), methyl 2-O-benzyl-3, 5-anhydro-α- and β-D-xylofuranoside (ⅦA, ⅦB)were obtained sequentially. The key intermediates both Ⅳ Aand Ⅵ Bare crystalline. The mass spectra of these compounds have been given.

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