Acetic acid (5R,5aS,8R,8aR)-5,7-diacetoxy-hexahydro-furo[3,2-e][1,4]dioxepin-8-yl ester | 852289-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: Acetic acid (5R,5aS,8R,8aR)-5,7-diacetoxy-hexahydro-furo[3,2-e][1,4]dioxepin-8-yl ester
• CAS: 852289-33-9
• 化学式: C₁₃H₁₈O₉
• 分子量: 318.281
• InChiKey: ZWEUQWXNYXJOCD-CEHFSTBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (5R,5aS,8R,8aR)-5,7-diacetoxy-hexahydro-furo[3,2-e][1,4]dioxepin-8-yl ester 、 2,4-二(三甲硅氧基)嘧啶 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以7 mg的产率得到(5R,5aS,7R,8R,8aS) acetic acid 5-acetoxy-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)hexahydrofuro[3,2-e][1,4]dioxepin-8-yl ester
  参考文献：
  名称：

  Bicyclic nucleoside analogues from d-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives

  摘要：

  The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3 '-O, and 5 '-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues. (c) 2005 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.007
• 作为产物：
  描述：

  (3aR,4R,5R,6R,6aR) [5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]acetic acid methyl ester 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 sodium periodate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 42.75h， 生成 Acetic acid (5R,5aS,8R,8aR)-5,7-diacetoxy-hexahydro-furo[3,2-e][1,4]dioxepin-8-yl ester
  参考文献：
  名称：

  Bicyclic nucleoside analogues from d-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives

  摘要：

  The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3 '-O, and 5 '-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues. (c) 2005 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.007