[(1R,4S,6R,7S,8R,9R,10R,12S,13S,16S,18S)-16-acetyloxy-6-[(3S)-3,4-dihydroxy-3-methylbutyl]-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-en-10-yl] benzoate | 404574-47-6

• 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: [(1R,4S,6R,7S,8R,9R,10R,12S,13S,16S,18S)-16-acetyloxy-6-[(3S)-3,4-dihydroxy-3-methylbutyl]-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-en-10-yl] benzoate
• CAS: 404574-47-6
• 化学式: C₃₆H₅₀O₇
• 分子量: 594.789
• InChiKey: QZPVPHHJLPFXHO-MJORLHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(1R,4S,6R,7S,8R,9R,10R,12S,13S,16S,18S)-16-acetyloxy-6-[(3S)-3,4-dihydroxy-3-methylbutyl]-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-en-10-yl] benzoate 在 咪唑 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 magnesium bromide ethyl etherate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2aS,4S,6aS,6bS,8R,8aR,8bR,9S,10R,11aS,12bR)-4-acetoxy-10-(3-(benzoyloxy)-4-hydroxy-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,9,10,11a,12b-hexadecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]furan-8-yl benzoate
  参考文献：
  名称：

  Synthesis of 14′,15′-dehydro-ritterazine Y via reductive and oxidative functionalizations of hecogenin acetate

  摘要：

  An analog of ritterazine Y was synthesized from hecogenin acetate in 23 steps via functional group manipulations of hecogenin acetate. Preparation of the north G and south Y units and the late stage Guo-Fuchs asymmetric coupling of the both units afforded the ritterazine Y analog. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.10.021
• 作为产物：
  描述：

  3β-acetoxy-12β-benzoyloxy-5α-furostan-14,26-diene 在 potassium osmate(VI) 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 18.0h， 生成 [(1R,4S,6R,7S,8R,9R,10R,12S,13S,16S,18S)-16-acetyloxy-6-[(3S)-3,4-dihydroxy-3-methylbutyl]-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-2-en-10-yl] benzoate
  参考文献：
  名称：

  Synthesis of 14′,15′-dehydro-ritterazine Y via reductive and oxidative functionalizations of hecogenin acetate

  摘要：

  An analog of ritterazine Y was synthesized from hecogenin acetate in 23 steps via functional group manipulations of hecogenin acetate. Preparation of the north G and south Y units and the late stage Guo-Fuchs asymmetric coupling of the both units afforded the ritterazine Y analog. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.10.021

文献信息

• Synthesis of C14,15-Dihydro-C22,25-<i>epi</i> North Unit of Cephalostatin 1 via “Red-Ox” Modifications of Hecogenin Acetate
  作者：Seongmin Lee、Daniel Jamieson、Philip L. Fuchs

  DOI：10.1021/ol802122p

  日期：2009.1.1

  The C14,15-Dihydro-C22,25-epi north unit of cephalostatin 1 has been synthesized in 11 operations from commercially available hecogenin acetate via multiple reductions and oxidations. The key transformations include (i) CrVI-catalyzed E-ring opening, (ii) C17 hydroxylation, and (iii) a base-triggered cyclization cascade.

  头孢抑素1的 C14,15-二氢-C22,25- epi北单元已在 11 次操作中从市售的醋酸hecogenin 通过多次还原和氧化合成。关键的转化包括 (i) Cr VI催化的 E 环打开，(ii) C17 羟基化和 (iii) 碱触发的环化级联反应。