[(2S,3S,4S,5R,6S)-2-[(2S,3Z,5S,6S,7S,8Z)-10-bromo-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-5,7,9-trimethyldeca-3,8-dienyl]-3,5-dimethyl-6-phenylsulfanyloxan-4-yl]oxy-tert-butyl-dimethylsilane | 184488-85-5

• 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: [(2S,3S,4S,5R,6S)-2-[(2S,3Z,5S,6S,7S,8Z)-10-bromo-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-5,7,9-trimethyldeca-3,8-dienyl]-3,5-dimethyl-6-phenylsulfanyloxan-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 184488-85-5
• 化学式: C₄₄H₈₁BrO₄SSi₃
• 分子量: 870.351
• InChiKey: RMKSEAPVNIICQA-BYZVUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.51
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4S,5R,6S)-2-[(2S,3Z,5S,6S,7S,8Z)-10-bromo-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-5,7,9-trimethyldeca-3,8-dienyl]-3,5-dimethyl-6-phenylsulfanyloxan-4-yl]oxy-tert-butyl-dimethylsilane 在 盐酸 、 aluminum oxide 、 lithium bis(dimethylphenylsilyl)amide 、 lithium tri-t-butoxyaluminum hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 84.17h， 生成 [(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-trihydroxy-19-[(2S,3R,4S,5R,6S)-4-hydroxy-3,5-dimethyl-6-phenylsulfanyloxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] carbamate
  参考文献：
  名称：

  Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization

  摘要：

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.

  DOI：

  10.1021/ja961374o
• 作为产物：
  描述：

  (2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol 在 palladium on activated charcoal 吗啉 、 吡啶 、 2,6-二甲基吡啶 、 chromium dichloride 、 lithium aluminium tetrahydride 、 草酰氯 、 18-冠醚-6 、 二甲基硫 、 氢氟酸 、 potassium tert-butylate 、 氢气 、 碘 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 臭氧 、 二甲基亚砜 、 三乙胺 、 lithium bromide 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 101.09h， 生成 [(2S,3S,4S,5R,6S)-2-[(2S,3Z,5S,6S,7S,8Z)-10-bromo-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-5,7,9-trimethyldeca-3,8-dienyl]-3,5-dimethyl-6-phenylsulfanyloxan-4-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization

  摘要：

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.

  DOI：

  10.1021/ja961374o

文献信息

• Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization
  作者：Deborah T. Hung、Jennie B. Nerenberg、Stuart L. Schreiber

  DOI：10.1021/ja961374o

  日期：1996.11.13

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.