(1S*,2R*,4S*,5R*)-2,4-bis(pivaloyloxymethyl)-3-oxabicyclo[4.3.0]non-7-en-1,5-diol | 244055-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S*,2R*,4S*,5R*)-2,4-bis(pivaloyloxymethyl)-3-oxabicyclo[4.3.0]non-7-en-1,5-diol
• 英文别名: [(1S,3R,3aS,7aR)-3-(2,2-dimethylpropanoyloxymethyl)-3a,7a-dihydroxy-1,3,4,7-tetrahydro-2-benzofuran-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 244055-77-4
• 化学式: C₂₀H₃₂O₇
• 分子量: 384.47
• InChiKey: GTTZIJGHKQAGCB-GOFCXKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S*,2R*,4S*,5R*)-2,4-bis(pivaloyloxymethyl)-3-oxabicyclo[4.3.0]non-7-en-1,5-diol 在 lead(IV) acetate 、 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 15.0h， 生成 2,2-Dimethyl-propionic acid (Z)-(2R,3R,8R,9S)-9-(2,2-dimethyl-propionyloxymethyl)-3,8-dihydroxy-2,3,4,7,8,9-hexahydro-oxonin-2-ylmethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy

  摘要：

  The extensive ring-expansion strategy for the synthesis of tetrahydrooxepin, oxocane, and hexahydrooxonin, which correspond to the D(E), I and F rings of ciguatoxin (CTX1B, 1), respectively, has been established. Chemoenzymatic acylation of the meso alcohols using a lipase provides an expeditious entry for the enantiomeric building blocks. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00370-1
• 作为产物：
  描述：

  [(2S,5R)-5-(2,2-dimethylpropanoyloxymethyl)-3,4-dimethylideneoxolan-2-yl]methyl 2,2-dimethylpropanoate 在 三乙烯二胺 、 四氧化锇 、 四丁基氟化铵 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲苯 、 叔丁醇 为溶剂， 反应 161.0h， 生成 (1S*,2R*,4S*,5R*)-2,4-bis(pivaloyloxymethyl)-3-oxabicyclo[4.3.0]non-7-en-1,5-diol
  参考文献：
  名称：

  Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy

  摘要：

  The extensive ring-expansion strategy for the synthesis of tetrahydrooxepin, oxocane, and hexahydrooxonin, which correspond to the D(E), I and F rings of ciguatoxin (CTX1B, 1), respectively, has been established. Chemoenzymatic acylation of the meso alcohols using a lipase provides an expeditious entry for the enantiomeric building blocks. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00370-1