Taxa-4(20),11(12)-dien-10β-tert-diethyl-iso-propylsilyloxy-2α,5α,14τriol | 444578-25-0

• 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: Taxa-4(20),11(12)-dien-10β-tert-diethyl-iso-propylsilyloxy-2α,5α,14τriol
• 英文别名: 10β-diethylisopropylsilyloxy-4(20),11-taxadiene-2α,5α,14β-triol；(1S,2S,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-2,5,14-triol
• CAS: 444578-25-0
• 化学式: C₂₇H₄₈O₄Si
• 分子量: 464.761
• InChiKey: GEQWZQYDDUPHLU-GVJOZBFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Taxa-4(20),11(12)-dien-10β-tert-diethyl-iso-propylsilyloxy-2α,5α,14τriol 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 62.17h， 生成 Taxa-4 (20),11(12)-dien-10β-diethyl-iso-propylsilyloxy-2,α 14β-di-S-methyldithiocarboxy-5α-ol
  参考文献：
  名称：

  Studies on Taxol Biosynthesis. Preparation of Taxa-4(20),11(12)-dien-5α-acetoxy-10β-ol by Deoxygenation of a Taxadiene Tetraacetate Obtained from Japanese Yew

  摘要：

  Taxa-4(20),11(12)-dien-5alpha-acetoxy-10beta-ol 6 has been identified as an early stage intermediate involved in the biosynthesis of taxol (Paclitaxel). This compound has been efficiently prepared by Barton deoxygenation of the C-2- and C-14-hydroxyl groups on a derivative semisynthetically prepared from taxa-4(20),11(12)-dien-2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl)butyrate (7), a major taxoid metabolite isolated from Japanese yew heart wood. The synthetic methodology is amenable for the preparation of isotopically labeled congeners that will be useful to probe further intermediate steps in the biosynthesis of taxol.

  DOI：

  10.1021/jo025679z
• 作为产物：
  描述：

  2α,5α,10β-triacetoxy-14β-(2'-methyl)-butysyloxy-4(20),11-taxadiene 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 119.0h， 生成 Taxa-4(20),11(12)-dien-10β-tert-diethyl-iso-propylsilyloxy-2α,5α,14τriol
  参考文献：
  名称：

  Studies on Taxol Biosynthesis. Preparation of Taxa-4(20),11(12)-dien-5α-acetoxy-10β-ol by Deoxygenation of a Taxadiene Tetraacetate Obtained from Japanese Yew

  摘要：

  Taxa-4(20),11(12)-dien-5alpha-acetoxy-10beta-ol 6 has been identified as an early stage intermediate involved in the biosynthesis of taxol (Paclitaxel). This compound has been efficiently prepared by Barton deoxygenation of the C-2- and C-14-hydroxyl groups on a derivative semisynthetically prepared from taxa-4(20),11(12)-dien-2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl)butyrate (7), a major taxoid metabolite isolated from Japanese yew heart wood. The synthetic methodology is amenable for the preparation of isotopically labeled congeners that will be useful to probe further intermediate steps in the biosynthesis of taxol.

  DOI：

  10.1021/jo025679z

文献信息

• 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
  作者：Tohru Horiguchi、Christopher D Rithner、Rodney Croteau、Robert M Williams

  DOI：10.1016/s0040-4020(02)01450-3

  日期：2003.1

  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.