(1S,2S,4S,7S,8R,9S,12S,13R,16S)-6-[(3R)-4-azido-3-methylbutyl]-16-[tert-butyl(diphenyl)silyl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-6-ol | 1307870-98-9

• 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: (1S,2S,4S,7S,8R,9S,12S,13R,16S)-6-[(3R)-4-azido-3-methylbutyl]-16-[tert-butyl(diphenyl)silyl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-6-ol
• CAS: 1307870-98-9
• 化学式: C₄₃H₆₁N₃O₃Si
• 分子量: 696.061
• InChiKey: BVBJNUVVCAAIBD-KFOJBIENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.57
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  87.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,4S,7S,8R,9S,12S,13R,16S)-6-[(3R)-4-azido-3-methylbutyl]-16-[tert-butyl(diphenyl)silyl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-6-ol 在 盐酸 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 8.0h， 生成 茄解定
  参考文献：
  名称：

  Total synthesis of solamargine

  摘要：

  Solamargine, (25R)-3 beta-{O-alpha-L-rhamnopyranosyl-(1 -> 2)-[O-alpha-L-rhamnopyranosyl-(1 -> 4)]-beta-D-glucopyranosyloxy}-22 alpha-N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC(50) ranging from 2.1 to 8.0 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.064
• 作为产物：
  描述：

  Acetic acid (2R,6S)-6-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxo-heptyl ester 在 sodium tetrahydroborate 、 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 20.0h， 生成 (1S,2S,4S,7S,8R,9S,12S,13R,16S)-6-[(3R)-4-azido-3-methylbutyl]-16-[tert-butyl(diphenyl)silyl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-6-ol
  参考文献：
  名称：

  Total synthesis of solamargine

  摘要：

  Solamargine, (25R)-3 beta-{O-alpha-L-rhamnopyranosyl-(1 -> 2)-[O-alpha-L-rhamnopyranosyl-(1 -> 4)]-beta-D-glucopyranosyloxy}-22 alpha-N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC(50) ranging from 2.1 to 8.0 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.064

文献信息

• 螺甾碱烷型糖苷生物碱的合成方法
  申请人：中国海洋大学

  公开号：CN103193858B

  公开（公告）日：2016-08-03

  本发明公开了一种螺甾碱烷型糖苷生物碱汇聚式化学合成方法，该方法包括如下步骤：(a)将3?位羟基用硅基或酰基保护的螺甾皂苷元(II)转化为相应的16?乙酰氧基?22?羰基?26?羟基胆甾烷(III)；(b)3?位羟基用硅基或酰基保护的16?乙酰氧基?22?羰基?26?磺酸酯胆甾烷的制备(IV)；(c)3?位羟基用硅基或酰基保护的16?乙酰氧基?22?羰基?26?叠氮基胆甾烷的制备(V)；(d)螺甾碱烷型皂苷元(VI)的制备；(e)酰基保护螺甾碱烷型糖苷生物碱的制备(VII)；(f)螺甾碱烷型糖苷生物碱(I)的制备。本发明的制备方法工艺简单，收率高，具有较强的实用价值。