(2S*,3S*,8R*,9R*)-(Z)-3,8-bis(trimethylsilylethoxymethoxy)oxon-5-en-2,9-dimethanol | 186656-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S*,3S*,8R*,9R*)-(Z)-3,8-bis(trimethylsilylethoxymethoxy)oxon-5-en-2,9-dimethanol
• 英文别名: [(2R,3R,5Z,8S,9S)-9-(hydroxymethyl)-3,8-bis(2-trimethylsilylethoxymethoxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methanol
• CAS: 186656-42-8
• 化学式: C₂₂H₄₆O₇Si₂
• 分子量: 478.774
• InChiKey: ZZNSOSSQFKUSND-KNFZPALDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S*,3S*,8R*,9R*)-(Z)-3,8-bis(trimethylsilylethoxymethoxy)oxon-5-en-2,9-dimethanol 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以72%的产率得到(2S*,3S*,8R*,9R*)-(Z)-2,9-bis(hydroxymethyl)-5-oxonen-3,8-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：

  (2R*,5S*)-2,5-bis(tert-butyldimethylsilyloxymethyl)-3,4-dimethylene-2,5-dihydrofuran 在 1,3-二噁烷 、 lead(IV) acetate 、 lithium hydroxide 、 sodium tetrahydroborate 、 四氧化锇 、 四丁基氟化铵 、 四丁基溴化铵 、 水 、 四丁基碘化铵 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 水 、 叔丁醇 、 苯 为溶剂， 反应 261.91h， 生成 (2S*,3S*,8R*,9R*)-(Z)-3,8-bis(trimethylsilylethoxymethoxy)oxon-5-en-2,9-dimethanol
  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

文献信息

• Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy
  作者：Tohru Oishi、Megumi Maruyama、Mitsuru Shoji、Kenji Maeda、Naomi Kumahara、Shin-ichiro Tanaka、Masahiro Hirama

  DOI：10.1016/s0040-4020(99)00370-1

  日期：1999.6

  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.