(E)-(4S,5R)-5-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-2-enoic acid ethyl ester | 321907-68-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(4S,5R)-5-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4S,5R)-5-[(2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyloxolan-2-yl]-5-hydroxy-2,4-dimethylpent-2-enoate
• CAS: 321907-68-0
• 化学式: C₁₆H₂₇BrO₅
• 分子量: 379.291
• InChiKey: RVHWQGHPIJPPGP-HUDLTUTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(4S,5R)-5-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-2-enoic acid ethyl ester 在 吡啶 、 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 二异丁基氢化铝 作用下， 生成 Methanesulfonic acid (1R,2S)-1-((2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-2-[(2R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-oxiranyl]-propyl ester
  参考文献：
  名称：

  Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans

  摘要：

  The use of a lactol methyl ether 23 in place of the simple tetrahydrofuran 11 allows for the high yielding non-aldol aldol process to occur without concomitant tetrahydropyran formation (cf 13) to give the desired product 24 in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01726-3
• 作为产物：
  描述：

  乙氧甲酰基亚乙基三苯基 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-(4S,5R)-5-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans

  摘要：

  The use of a lactol methyl ether 23 in place of the simple tetrahydrofuran 11 allows for the high yielding non-aldol aldol process to occur without concomitant tetrahydropyran formation (cf 13) to give the desired product 24 in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01726-3

文献信息

• Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans
  作者：Michael E Jung、Christopher P Lee

  DOI：10.1016/s0040-4039(00)01726-3

  日期：2000.12

  The use of a lactol methyl ether 23 in place of the simple tetrahydrofuran 11 allows for the high yielding non-aldol aldol process to occur without concomitant tetrahydropyran formation (cf 13) to give the desired product 24 in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.