3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide | 292068-65-6

• 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: 3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide
• 英文别名: 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-3-[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-tri(propan-2-yl)silyloxyoxan-2-yl]oxy-1,5,11,14-tetrahydroxy-13-methyl-10-[tri(propan-2-yl)silyloxymethyl]-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 292068-65-6
• 化学式: C₄₇H₈₄O₁₂Si₂
• 分子量: 897.348
• InChiKey: IOSNNHVYZWARFA-YEESGZDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  185
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以82%的产率得到3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-5,14-dihydroxy-1,11-dioxocard-20(22)-enolide
  参考文献：
  名称：

  Regioselective derivatization of ouabain with trialkylsilyl reagents and selective oxidation of the unprotected alcohols

  摘要：

  Many mammalian tissues contain cardiac glycoside-like steroids that inhibit the sodium pump. A ouabain-like compound has been described in the human circulation and suggested to be ouabain or a closely related isomer. Ouabain is a highly hydroxylated compound and one of the most potent inhibitors of the sodium pump. Trialkylsilyl derivatization of ouabain has been carried out to determine reagent selectivity among the eight hydroxy groups as a prelude to the synthesis of regiospecific isomers, Mono-, di-, tri-, and hexa-trialkylsilyl derivatives have been prepared with substitution at the 19-, the 3',19-, the 1,3',19-, and the 1,2',3',4',11,19-positions, respectively. Mass spectrometry and NMR confirmed the substitutions. Selective protection of the hydroxy groups allows selective oxidation of the unprotected steroid ring alcohols without oxidation of the 2'- and 4'-rhamnoside alcohols. Pyridinium dichromate oxidation of the di-trialkylsilyl and tri-trialkylsilyl derivatives gave the 1,1 I-diketone and the 1 I-ketone analogues, respectively. These regioselective reactions open a route to the synthesis of a series of closely related isomers of ouabain and other derivatives that may have useful structure-activity relationships and utility in the elucidation of the biosynthesis of ouabain-like compounds. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00096-9
• 作为产物：
  描述：

  G毒毛旋花苷 、 三异丙基硅基三氟甲磺酸酯 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以88%的产率得到3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide
  参考文献：
  名称：

  Regioselective derivatization of ouabain with trialkylsilyl reagents and selective oxidation of the unprotected alcohols

  摘要：

  Many mammalian tissues contain cardiac glycoside-like steroids that inhibit the sodium pump. A ouabain-like compound has been described in the human circulation and suggested to be ouabain or a closely related isomer. Ouabain is a highly hydroxylated compound and one of the most potent inhibitors of the sodium pump. Trialkylsilyl derivatization of ouabain has been carried out to determine reagent selectivity among the eight hydroxy groups as a prelude to the synthesis of regiospecific isomers, Mono-, di-, tri-, and hexa-trialkylsilyl derivatives have been prepared with substitution at the 19-, the 3',19-, the 1,3',19-, and the 1,2',3',4',11,19-positions, respectively. Mass spectrometry and NMR confirmed the substitutions. Selective protection of the hydroxy groups allows selective oxidation of the unprotected steroid ring alcohols without oxidation of the 2'- and 4'-rhamnoside alcohols. Pyridinium dichromate oxidation of the di-trialkylsilyl and tri-trialkylsilyl derivatives gave the 1,1 I-diketone and the 1 I-ketone analogues, respectively. These regioselective reactions open a route to the synthesis of a series of closely related isomers of ouabain and other derivatives that may have useful structure-activity relationships and utility in the elucidation of the biosynthesis of ouabain-like compounds. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00096-9