ethyl 2-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]acetate | 74348-77-9

• 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: ethyl 2-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]acetate
• CAS: 74348-77-9
• 化学式: C₂₄H₃₈O₃
• 分子量: 374.564
• InChiKey: UADRPJFDXVLOIP-HXLLTLRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]acetate 在 吡啶 、 lithium aluminium tetrahydride 、 水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-4-((R)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)butan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
  参考文献：
  名称：

  Use of malic acid as a chiral synthon: 24,25-Dihydroxycholecalciferol

  摘要：

  DOI：

  10.1016/s0040-4039(00)95394-2
• 作为产物：
  描述：

  在 铂 氢气 作用下， 以 乙醇 为溶剂， 生成 ethyl 2-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]acetate
  参考文献：
  名称：

  Wicha,J. et al., Polish Journal of Chemistry, 1979, vol. 53, p. 2643 - 2645

  摘要：

  DOI：

文献信息

• Synthesis of (23R)- and (23S)-23H-Isocalysterols, Marine Sterols with a Cyclopropene Moiety in the Side Chain
  作者：Alicja Kurek-Tyrlik、Kazimierz Minksztym、Jerzy Wicha

  DOI：10.1002/(sici)1099-0690(200003)2000:6<1027::aid-ejoc1027>3.0.co;2-e

  日期：2000.3

  A synthesis of (23R)- and (23S)-23H-calysterols 2a and 2b from pregnanoic ester 10 is reported. Alkylation of 10 with dibromide 19b, followed by reduction of the carboethyloxy group to a methyl group, afforded (Z)-vinylic bromide 22. Dibromocyclopropanation of 22 yielded the diastereomeric tribromocyclopropane derivatives 15c and 15d. The corresponding 3-hydroxy-5-ene 17c was transformed into 2a via

  报道了从孕烷酸酯 10 合成 (23R)-和 (23S)-23H-calysterols 2a 和 2b。10 用二溴化物 19b 烷基化，然后将碳乙氧基还原为甲基，得到 (Z)-乙烯基溴化物 22。22 的二溴环丙烷化得到非对映异构体三溴环丙烷衍生物 15c 和 15d。相应的 3-羟基-5-烯 17c 通过 25 和环丙烯基锂中间体转化为 2a。还研究了涉及乙烯基硅烷 13 和 (E)-乙烯基溴 14 的替代合成路线。
• Synthesis of dimeric steroids as components of lipid membranes
  作者：Jacek W. Morzycki、Sławomir Kalinowski、Zenon Łotowski、Joanna Rabiczko

  DOI：10.1016/s0040-4020(97)00669-8

  日期：1997.7

  The synthesis of three dimeric steroids 1,2, and 3, as components of artificial lipid bilayer membranes, is described. Di(3β-hydroxyfurost-5-en-26-yl) (1) was obtained from diosgenin by reductive fission of a ring F, substitution of -OH by -l, and the Wurtz reaction. Two other dimers 2 and 3 were synthesised from the pregnanoic ester 10 by an “alkylation-reduction” procedure.

  描述了作为人工脂质双层膜成分的三种二聚体甾体1,2和3的合成。由薯F皂苷元通过环F的还原裂变，-OH被-l取代和Wurtz反应而获得二（3β-羟基糠醛-5-en-26-基）（1）。通过“烷基化-还原”方法由孕烷酸酯10合成另外两个二聚体2和3。
• Towards Synthesis of Calysterols, Marine Sterols with Cyclopropene Moiety in the Side Chain: Synthesis of 26,27-Dinor-23H-isocalysterol
  作者：Alicja Kurek-Tyrlik、Kazimierz Minksztym、Jerzy Wicha

  DOI：10.1135/cccc19981575

  日期：——

  26,27-Dinor-23H-isocalysterol 24 has been synthesized in 19% yield (6 steps) from ethyl 6β-methoxy-3α,5-cyclo-5α-pregnan-21-oate (18). For construction of the side chain, alkylation of lithium salt of ester 18 with 1-bromo-1,2-dimethyl-c-3-iodomethyl-c-2-(trimethylsilyl)cyclopropane 16 was used. It has been shown that reduction of the ester group in position 21 and rearrangement of the 3,5-cyclosteroid system are compatible with the sidechain functionalities. It has been found that methylation of 1,1-dibromo-2-(trimethylsilyl)cyclopropane is accompanied by an rearrangement involving 1,2-migration of the trimethylsilyl group.

  26,27-Dinor-23H-isocalysterol 24已经从乙酸乙酯6β-甲氧基-3α,5-环-5α-孕酮-21-酸酯（18）中合成，收率为19％（6步）。为了构建侧链，使用1-溴-1,2-二甲基-c-3-碘甲基-c-2-（三甲基硅基）环丙烷16的乙酸锂盐烷基化乙酸酯18。已经证明，21位酯基还原和3,5-环甾体系统重排与侧链功能相兼容。发现1,1-二溴-2-（三甲基硅基）环丙烷的甲基化伴随着涉及三甲基硅基团1,2-迁移的重排。