(1R,3aR,5R,6S,6aR) 1-[6-(2-hydroxyethoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethan-1,2-diol | 852289-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3aR,5R,6S,6aR) 1-[6-(2-hydroxyethoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethan-1,2-diol
• CAS: 852289-25-9
• 化学式: C₁₁H₂₀O₇
• 分子量: 264.276
• InChiKey: WIJUSODZAFWOPE-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,3aR,5R,6S,6aR) 1-[6-(2-hydroxyethoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethan-1,2-diol 在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以80%的产率得到(3aR,3bS,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
• 作为产物：
  描述：

  (3aR,4R,5R,6S,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 甲醇 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 水 、 叔丁醇 为溶剂， 反应 13.0h， 生成 (1R,3aR,5R,6S,6aR) 1-[6-(2-hydroxyethoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethan-1,2-diol
  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