(Z)-(4S,5R,6S,7R)-7-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-7-methanesulfonyloxy-4,6-dimethyl-hept-2-enoic acid methyl ester | 321907-71-5

• 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: (Z)-(4S,5R,6S,7R)-7-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-7-methanesulfonyloxy-4,6-dimethyl-hept-2-enoic acid methyl ester
• 英文别名: methyl (Z,4S,5R,6S,7R)-7-[(2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyloxolan-2-yl]-5-hydroxy-4,6-dimethyl-7-methylsulfonyloxyhept-2-enoate
• CAS: 321907-71-5
• 化学式: C₁₈H₃₁BrO₈S
• 分子量: 487.409
• InChiKey: WCNOUNJBHPTDQV-XBLNGTSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3R)-3-((2S,3R,4S)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-2-methyl-3-trimethylsilanyloxy-propionaldehyde 在 吡啶 、 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (Z)-(4S,5R,6S,7R)-7-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-7-methanesulfonyloxy-4,6-dimethyl-hept-2-enoic acid methyl 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.