10β-diethylisopropylsilyloxytaxa-4(20),11-dien-5α,14β-diol | 503313-19-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 10β-diethylisopropylsilyloxytaxa-4(20),11-dien-5α,14β-diol
• 英文别名: (1S,3S,5S,8S,10S,14S)-10-[diethyl(propan-2-yl)silyl]oxy-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.03,8]pentadec-11-ene-5,14-diol
• CAS: 503313-19-7
• 化学式: C₂₇H₄₈O₃Si
• 分子量: 448.762
• InChiKey: VUFPRFVVKDHXGO-MNFMZPDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  10β-diethylisopropylsilyloxytaxa-4(20),11-dien-5α,14β-diol 在 氟化氢吡啶 作用下， 以 吡啶 为溶剂， 反应 4.0h， 以94%的产率得到taxa-4(20),11-dien-5α,10β,14β-triol
  参考文献：
  名称：

  Studies on taxol biosynthesis. Preparation of 5α-acetoxytaxa-4(20),11-dien-2α,10β-diol derivatives by deoxygenation of a taxadiene tetra-acetate obtained from Japanese yew

  摘要：

  The putative metabolite, 5alpha-acetoxytaxa-4(20),11-dien-2alpha,10beta-diol (7), which is a promising candidate as a biosynthetic pathway triol in taxol biosynthesis, has been prepared by Barton deoxygenation of the C-14-hydroxyl group of a differentially protected derivative of natural 2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl)-butyryloxytaxa-4(20),11-diene (8), a major taxoid metabolite isolated from Japanese Yew heart wood. The synthetic protocol devised, is amenable for the preparation of isotopically labeled congeners that will be useful to probe further intermediate steps in the biosynthesis of taxol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01450-3
• 作为产物：
  描述：

  [(1S,2S,3S,5S,8S,10S,14S)-10-[diethyl(propan-2-yl)silyl]oxy-5,14-dihydroxy-8,12,15,15-tetramethyl-4-methylidene-2-tricyclo[9.3.1.03,8]pentadec-11-enyl]oxy-phenoxymethanethione 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 10β-diethylisopropylsilyloxytaxa-4(20),11-dien-5α,14β-diol
  参考文献：
  名称：

  Studies on taxol biosynthesis. Preparation of 5α-acetoxytaxa-4(20),11-dien-2α,10β-diol derivatives by deoxygenation of a taxadiene tetra-acetate obtained from Japanese yew

  摘要：

  The putative metabolite, 5alpha-acetoxytaxa-4(20),11-dien-2alpha,10beta-diol (7), which is a promising candidate as a biosynthetic pathway triol in taxol biosynthesis, has been prepared by Barton deoxygenation of the C-14-hydroxyl group of a differentially protected derivative of natural 2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl)-butyryloxytaxa-4(20),11-diene (8), a major taxoid metabolite isolated from Japanese Yew heart wood. The synthetic protocol devised, is amenable for the preparation of isotopically labeled congeners that will be useful to probe further intermediate steps in the biosynthesis of taxol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01450-3