5,6-dideoxy-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-hept-5-enofuranurono-7,3-lactone | 1221276-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 5,6-dideoxy-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-hept-5-enofuranurono-7,3-lactone
• 英文别名: (1S,2R,4S,6R,8R)-4-(trichloromethyl)-3,5,7,12-tetraoxatricyclo[6.4.0.02,6]dodec-9-en-11-one
• CAS: 1221276-84-1
• 化学式: C₉H₇Cl₃O₅
• 分子量: 301.511
• InChiKey: GJMQVHBHQAFGLX-BIAPBZAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-3-[(2S,3aR,5R,6S,6aR)-6-hydroxy-2-(trichloromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5,6-dideoxy-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-hept-5-enofuranurono-7,3-lactone
  参考文献：
  名称：

  Selective Wittig olefination in aqueous media for the rapid preparation of unsaturated 7,3-lactone-α-d-xylofuranose derivatives

  摘要：

  A highly efficient and rapid protocol for the preparation of the title compounds 1a and 1b from D-glucose derivatives 2a and 2b, respectively, is reported. To this end, highly selective Wittig olefination in aqueous media was developed for the elaboration of alpha,beta-unsaturated acids 5a and 5b, which when treated with DCC, lactonization was accomplished and the title compounds 1a and 1b were obtained in only three sequential steps with overall yields of 85% and 88%, respectively. Additionally, the Z-selectivity was studied by analyzing conformational models of its corresponding oxophosphorinane intermediaries. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.094