(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 | 475051-51-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (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
• 英文别名: ethyl (Z,2R,3S,5S,8S,9S,10S)-2-bromo-5,9-bis[[tert-butyl(dimethyl)silyl]oxy]-11-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-2,8,10-trimethylundec-6-enoate
• CAS: 475051-51-5
• 化学式: C₄₄H₇₅BrO₆Si₃
• 分子量: 864.236
• InChiKey: QXOLTEFSXGVAHP-KVXZAUCMSA-N

物化性质

• 沸点：
  717.9±60.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.64
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 2,6-二甲基吡啶 、 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 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)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol 在 chiral borane from L-TsVal 硼烷四氢呋喃络合物 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (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
  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

文献信息

• A straightforward, highly stereoselective construction of eight stereogenic centers in (+)-discodermolide C1–C13 segment, based on a strategy of iterative aldol reactions
  作者：Kazi A. Shahid、Jahan Mursheda、Momotoshi Okazaki、Yoshihiro Shuto、Fumitaka Goto、Syun-ichi Kiyooka

  DOI：10.1016/s0040-4039(02)01389-8

  日期：2002.9

  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.