(22R,25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxyfurost-5-en-22-ol | 1164104-12-4

• 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: (22R,25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxyfurost-5-en-22-ol
• CAS: 1164104-12-4
• 化学式: C₃₅H₆₀O₅Si
• 分子量: 588.944
• InChiKey: XGZHXTUQCIMJPY-ZXGZWFALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (22R,25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxyfurost-5-en-22-ol 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(R)-4-((4S,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-4-hydroxy-10-methoxy-6a,8a,9-trimethyl-3,4,5,6,6a,6b,7,8,8a,8b,9,10,11a,12,12a,12b-hexadecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]furan-10-yl)-2-methylbutyl acetate
  参考文献：
  名称：

  Synthesis and cytotoxicities of icogenin analogues with disaccharide residues

  摘要：

  For further structure-activity relationships (SAR) research of furostan saponin, two icogenin analogues: (25R)-22-O-methyl-furost-5-en-3 beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside 1 and (25R)-22-O-methyl-furost-5-en-3 beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-glucopyranoside 2, with valuable disaccharide moieties, were synthesized from diosgenin through eight steps. Both of the analogues behaved the similar cytotoxic activities with icogenin, towards nine types of human tumor cells herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.092
• 作为产物：
  描述：

  (25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxycholest-5-ene-16,22-dione 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以36%的产率得到(22R,25R)-26-acetyloxy-3β-tert-butyldimethylsilyloxyfurost-5-en-22-ol
  参考文献：
  名称：

  Synthesis and cytotoxicities of icogenin analogues with disaccharide residues

  摘要：

  For further structure-activity relationships (SAR) research of furostan saponin, two icogenin analogues: (25R)-22-O-methyl-furost-5-en-3 beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside 1 and (25R)-22-O-methyl-furost-5-en-3 beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-glucopyranoside 2, with valuable disaccharide moieties, were synthesized from diosgenin through eight steps. Both of the analogues behaved the similar cytotoxic activities with icogenin, towards nine types of human tumor cells herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.092

文献信息

• The synthesis of cholestane and furostan saponin analogues and the determination of sapogenin's absolute configuration at C-22
  作者：Haixing Wang、Yanshen Guo、Yuyao Guan、Liang Zhou、Pingsheng Lei

  DOI：10.1016/j.steroids.2010.07.011

  日期：2011.1

  ucopyranoside] 26, were synthesized ultimately. The structures of all the synthesized analogues were confirmed by spectroscopic methods. The S-chirality at C-22 of cholestane was confirmed by Mosher's method. The absolute configuration at C-22 of furostan saponin analogues was distinguished by conformational analysis combined with the NMR spectroscopy. The cytotoxicities of the synthetic analogues

  首次建立并采用了一种简便有效的合成胆甾烷和呋甾皂苷类似物的方法。遵循这一策略，从薯蓣皂苷元开始，三种新型胆甾烷皂苷类似物：(22S,25R)-3β,22,26-trihydroxy-cholest-5-ene-16-one 22-O-[O-α-L-rhamnopyranosyl- (1→2)-β-D-吡喃葡萄糖苷] 11, (25R)-3β,16β,26-trihydroxy-cholest-5-ene-22-one 16-O-[O-α-L-rhamnopyranosyl-(1 →2)-α-D-吡喃葡萄糖苷] 14 和 (25R)-3β,16β,26-trihydroxy-cholest-5-ene-22-one 16-O-[O-α-L-rhamnopyranosyl-(1→2 )-β-D-吡喃葡萄糖苷] 17、三种新型呋喃坦皂苷类似物：(22S,25R)-furost-5-ene-3β,22