(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester | 475051-55-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester
• CAS: 475051-55-9
• 化学式: C₄₂H₆₈O₇Si₂
• 分子量: 741.169
• InChiKey: IPJGGWZIAYGHMR-SZFAKFBISA-N

物化性质

• 沸点：
  698.6±55.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.11
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester 在 2,6-二甲基吡啶 作用下， 以97%的产率得到ethyl (2R,3S,4S,5S,7S,8Z,10S,11S,12S)-3,11-(tert-butyldimethylsiloxy)-13-(tert-butyldiphenylsiloxy)-2,4,10,12-tetramethyl-5,7-methylenedioxy-8-tridecenoate
  参考文献：
  名称：

  A straightforward, highly stereoselective construction of eight stereogenic centers in (+)-discodermolide C1–C13 segment, based on a strategy of iterative aldol reactions

  摘要：

  The eight stereogenic centers were introduced into the C-1-C-13 segment of (+)-discodermolide by iterative aldol reactions with quite a high level of selection. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01389-8
• 作为产物：
  描述：

  (Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-5,9-bis-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,8,10-trimethyl-undec-6-enoic acid ethyl ester 在 三乙基硼 、 三正丁基氢锡 、 phosphorus pentoxide 、 四氯化钛 、 二异丁基氢化铝 、 magnesium bromide 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 22.5h， 生成 (2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  A straightforward, highly stereoselective construction of eight stereogenic centers in (+)-discodermolide C1–C13 segment, based on a strategy of iterative aldol reactions

  摘要：

  The eight stereogenic centers were introduced into the C-1-C-13 segment of (+)-discodermolide by iterative aldol reactions with quite a high level of selection. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01389-8