(2S*,3R*,6S*,7R*)-2,7-bis(triisopropylsilyloxymethyl)-3,6-bis(benzyloxymethyloxy)-2,3,6,7-tetrahydrooxepin | 244055-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S*,3R*,6S*,7R*)-2,7-bis(triisopropylsilyloxymethyl)-3,6-bis(benzyloxymethyloxy)-2,3,6,7-tetrahydrooxepin
• 英文别名: [(2R,3S,6R,7S)-3,6-bis(phenylmethoxymethoxy)-7-[tri(propan-2-yl)silyloxymethyl]-2,3,6,7-tetrahydrooxepin-2-yl]methoxy-tri(propan-2-yl)silane
• CAS: 244055-69-4
• 化学式: C₄₂H₇₀O₇Si₂
• 分子量: 743.185
• InChiKey: GTBMKMPJWGQISE-RTYOPHJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.81
• 重原子数：
  51
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S*,3R*,6S*,7R*)-2,7-bis(triisopropylsilyloxymethyl)-3,6-bis(benzyloxymethyloxy)-2,3,6,7-tetrahydrooxepin 在 palladium dihydroxide palladium diacetate 、 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 20.0 ℃ 、98.06 kPa 条件下， 反应 32.0h， 生成 (1R*,2S*,3R*,5S*,6R*,7S*,8R*)-3,5-bis(triisopropylsilyloxymethyl)-8-methyl-4-oxabicyclo[5.1.0]octan-2,6-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
• 作为产物：
  描述：

  (2S*,7R*)-2,7-bis(triisopropylsilyloxymethyl)oxepan-3,6-dione 在 三乙基硅烷 、 三甲基氯硅烷 、 四氯化钛 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 (2S*,3R*,6S*,7R*)-2,7-bis(triisopropylsilyloxymethyl)-3,6-bis(benzyloxymethyloxy)-2,3,6,7-tetrahydrooxepin
  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