Methanesulfonic acid (E)-(1R,2S)-1-((2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-3-enyl ester | 321907-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (E)-(1R,2S)-1-((2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-3-enyl ester
• 英文别名: [(E,1R,2S)-1-[(2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyloxolan-2-yl]-5-hydroxy-2,4-dimethylpent-3-enyl] methanesulfonate
• CAS: 321907-69-1
• 化学式: C₁₅H₂₇BrO₆S
• 分子量: 415.346
• InChiKey: YZBYHESXQWJFRU-OXCAYMBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (E)-(1R,2S)-1-((2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-3-enyl ester 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-(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
• 作为产物：
  描述：

  (3S,4R,5S)-4-Bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-dihydro-furan-2-one 在 吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 四丁基氟化铵 、 二异丁基氢化铝 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (E)-(1R,2S)-1-((2S,3R,4S,5R)-3-bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-5-hydroxy-2,4-dimethyl-pent-3-enyl 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.