(3aR,3bR,8S,8aS,9aR) 2,2-dimethyl-hexahydro-1,3,4,7,9-pentaoxa-cyclopenta[a]azulen-8-ol | 852289-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aR,3bR,8S,8aS,9aR) 2,2-dimethyl-hexahydro-1,3,4,7,9-pentaoxa-cyclopenta[a]azulen-8-ol
• 英文别名: (1R,2R,6R,8S,9S)-4,4-dimethyl-3,5,7,10,13-pentaoxatricyclo[6.5.0.02,6]tridecan-9-ol
• CAS: 852289-32-8
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: OHZQVQJJFYWUQZ-QKCLAQEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,3bR,8S,8aS,9aR) 2,2-dimethyl-hexahydro-1,3,4,7,9-pentaoxa-cyclopenta[a]azulen-8-ol 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 35.0h， 生成 (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：

  在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以33 mg的产率得到(3aR,3bR,8S,8aS,9aR) 2,2-dimethyl-hexahydro-1,3,4,7,9-pentaoxa-cyclopenta[a]azulen-8-ol
  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