(R)-3-[(3S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butan-1-ol | 69454-98-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (R)-3-[(3S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butan-1-ol
• CAS: 69454-98-4
• 化学式: C₂₉H₅₂O₂Si
• 分子量: 460.816
• InChiKey: HLKVIBCPWUSZNC-OHPSOFBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-3-[(3S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以0.23 g的产率得到(3β,20R)-3-<(tert-butyldimethylsilyl)oxy>-24-norchol-5-en-23-al
  参考文献：
  名称：

  Synthesis of 23-ketocholestane derivatives with different side-chain lengths (asterosapogenin analogs)

  摘要：

  Syntheses were developed for 23-ketoasterosapogenin analogs with various side-chain lengths from dimethyl(tert-butyl)silyloxypregnenolone (DMTBS-pregnenolone) through 20-hydroxy-23-carboxylates or 22-acetylenic (C5, C6) derivatives by reduction and allylic rearrangement with concurrent oxidation of the intermediate 23-hydroxy-27-nor- and 27-nor-26-methylcholestanes.

  DOI：

  10.1007/bf00958594
• 作为产物：
  描述：

  (3β,20R)-3-<(tert-butyldimethylsilyl)oxy>-24-norchol-5-en-23-al 在 borane tert-butylamine 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以100%的产率得到(R)-3-[(3S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butan-1-ol
  参考文献：
  名称：

  Synthesis, specificity, and antifungal activity of inhibitors of the Candida albicans .DELTA.24-sterol methyltransferase

  摘要：

  A series of side chain modified analogues of cholesterol and lanosterol (1-10) have been synthesized and evaluated as inhibitors of the Candida albicans DELTA-24-sterol methyltransferase. Two sterol substrate analogues 1 and 2 which contained a 24-thia substituent were relatively modest inhibitors of the enzyme (K(i) = 1.5-72-mu-M). Compounds which mimic the carbocation intermediates proposed for the methyltransferase reaction, including sulfonium salts 4-6, amidines 7 and 8, and imidazoles 9 and 10 were substantially more potent inhibitors (K(i) = 5-500 nM). All of the sterol analogues examined displayed less than 10-fold selectivity for inhibition of the methyltransferase versus the rat liver DELTA-24-sterol reductase. The sterol analogues were tested for in vitro antifungal activity against C. albicans, Candida tropicalis, and Torulopsis glabrata. The minimum inhibitory concentrations versus C. albicans correlated well with the K(i) values for methyltransferase inhibition, and the potency of several compounds approached that of amphotericin B, although only modest fungicidal activity was observed.

  DOI：

  10.1021/jm00079a012

文献信息

• Syntheses of cholesterol analogs with a carbene-generating substituent on the side chain.
  作者：Takeshi Terasawa、Nobuo Ikekawa、Masuo Morisaki

  DOI：10.1248/cpb.34.931

  日期：——

  As photoaffinity-labelled analogs of cholesterol, the diazoacetate 1__∼, the aryldiazirines 2__∼ and 3__∼, and the fluorodiazirine 4__∼ were prepared.

  作为胆固醇的光亲和标记类似物，制备了重氮乙酸酯 1__∼、芳基二氮丙啶 2__∼和 3__∼以及氟二氮丙啶 4__∼。