6β-methoxy-3α,5-cyclocholestan-24-ol | 66461-41-4

• 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: 6β-methoxy-3α,5-cyclocholestan-24-ol
• CAS: 66461-41-4
• 化学式: C₂₈H₄₈O₂
• 分子量: 416.688
• InChiKey: SVMSFQNAFFCXJI-WFUZEJEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  6β-methoxy-3α,5-cyclocholestan-24-ol 在 二乙胺基三氟化硫 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 24ξ-flourocholesterol
  参考文献：
  名称：

  Side chain modified sterols as probes into insect molting hormone metabolism. II: Synthesis of monofluorocholesterols

  摘要：

  The hydroxylations of the cholesterol side chain at C-20, 22, and 25 are key terminal events in ecdysone biogenesis. We have prepared the C-20, C-22, C-24, and C-25 monofluorinated cholesterols as potential inhibitors of these hydroxylation events, and preliminary bioassay results in Manduca sexta are reported. The synthesis of [26(14)C]-20-fluorocholesterol is also described. Although the 20-, 22-, and 25-monofluorocholesterols do not appear to affect larval growth and development, the 24-fluoro isomer shows a moderate retardation of growth and a modest increase in mortality.

  DOI：

  10.1016/0039-128x(83)90018-1
• 作为产物：
  描述：

  (22E)-6β-methoxy-3α,5α-cyclocholest-5,22-dien-24-ol 在 platinum on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 6β-methoxy-3α,5-cyclocholestan-24-ol
  参考文献：
  名称：

  Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol

  摘要：

  The chiral beta-amino alcohols-catalyzed addition of diisopropylzinc to steroidal 24-aldehydes successfully provided 24(R)-hydroxycholesterols in good yields with high diastereoselectivities, which are synthetic intermediates of 1 alpha,24(R)-dihydroxyvitamin D-3 (1). alpha,beta-Unsaturated steroidal aldehydes were found to give the corresponding isopropylated adducts in much higher yields (up to 91%) than those of saturated steroidal aldehydes.

  DOI：

  10.1016/0957-4166(95)00073-x

文献信息

• Stereochemical fate of the isopropylidene methyl groups of lanosterol during the biosynthesis of isofucosterol in Pinus pinea
  作者：Francesco Nicotra、Fiamma Ronchetti、Giovanni Russo、Giuseppe Lugaro、Marilena Casellato

  DOI：10.1039/p19810000498

  日期：——

  [26-3H]Lanosterol (16) was administered to Pinus pinea and the [26-3H]isofucosteryl acetate (6) obtained was chemically transformed into [26-3H]cholesterol (13). Compound (13) was incubated with rat-liver mitochondria to yield [3-3H] propionic acid. The data obtained are consistent with a biosynthetic pathway in which the pro-E isopropylidene methyl group of the Δ24-precursor becomes the pro-R isopropyl

  [26- 3 H]羊毛甾醇（16）中的溶液施用至松pinea和[26- 3 H]乙酸isofucosteryl（6）中得到的化学转化成[26- 3 H]胆固醇（13）。将化合物（13）与大鼠肝线粒体一起温育以产生[3- 3 H]丙酸。获得的数据是具有生物合成途径相一致，其中所述亲的Δ的-E异亚甲基24 -precursor变为亲-R异丙基甲基组中isofucosterol。