Acetic acid (3aR,3bS,4R,5S,7aR,8S,8aR)-3a,5-dihydroxy-4-hydroxymethyl-2,2,7a-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester | 220487-49-0

• 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: Acetic acid (3aR,3bS,4R,5S,7aR,8S,8aR)-3a,5-dihydroxy-4-hydroxymethyl-2,2,7a-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester
• 英文别名: [(1Z,3aR,4S,4aR,7S,8R,8aS,8bR)-7,8b-dihydroxy-8-(hydroxymethyl)-2,2,4a-trimethyl-1-[2-(2-methyl-1,3-dioxolan-2-yl)ethylidene]-3,3a,4,7,8,8a-hexahydrocyclopenta[a]inden-4-yl] acetate
• CAS: 220487-49-0
• 化学式: C₂₄H₃₆O₇
• 分子量: 436.546
• InChiKey: GVBLIIDHVUSAPQ-BKWVKVISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aR,3bS,4R,5S,7aR,8S,8aR)-3a,5-dihydroxy-4-hydroxymethyl-2,2,7a-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester 在 叔丁基过氧化氢 、 sodium hydroxide 、 bis(acetylacetonate)oxovanadium 、 2,2-DMP 、 对甲苯磺酸 作用下， 以 甲醇 、 癸烷 、 水 、 苯 为溶剂， 反应 0.66h， 生成
  参考文献：
  名称：

  Studies towards the total synthesis of taxoids The aldol-annelation-fragmentation strategy

  摘要：

  We describe an aldol-annelation-fragmentation strategy culminating in the stereoselective synthesis of the whole 20-carbon A-seco taxane framework 1 in only 12 linear steps starting from the two achiral aldol partners 2 and 3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10703-1
• 作为产物：
  描述：

  Acetic acid (3aR,3bS,7aR,8S,8aR)-3a-hydroxy-2,2,7a-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-5-oxo-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester 在 2,3,5-三甲基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 四丁基氟化铵 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 Acetic acid (3aR,3bS,4R,5S,7aR,8S,8aR)-3a,5-dihydroxy-4-hydroxymethyl-2,2,7a-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester
  参考文献：
  名称：

  Studies towards the total synthesis of taxoids The aldol-annelation-fragmentation strategy

  摘要：

  We describe an aldol-annelation-fragmentation strategy culminating in the stereoselective synthesis of the whole 20-carbon A-seco taxane framework 1 in only 12 linear steps starting from the two achiral aldol partners 2 and 3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10703-1

文献信息

• Studies towards the total synthesis of taxoids: a rapid entry into bicyclo[6.4.0]dodecane ring system. Part 1
  作者：Siméon Arseniyadis、Marı́a del Rosario Rico Ferreira、José Quı́lez del Moral、José Ignacio Martı́n Hernando、Pierre Potier、Loı̈c Toupet

  DOI：10.1016/s0957-4166(98)00434-0

  日期：1998.11

  We report a short and stereocontrolled synthesis of the taxoid BC-subunit (+)-5 embodying the whole carbon framework and most of the required oxygen functionalities for further elaboration. Enantiomeric purity was secured at an early stage by resolution involving derivatization with (S)-2-acetoxypropionyl chloride on (+/-)-10b. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Arseniyadis, Simeon; Alves, Rosemeire Brondi; De Freitas, Rossimiriam Pereira, Heterocycles, <hi>1997</hi>, vol. 46, # 1, p. 727 - 764
  作者：Arseniyadis, Simeon、Alves, Rosemeire Brondi、De Freitas, Rossimiriam Pereira、Dorado, Manuel Munoz、Yashunsky, Dmitry V.、Potier, Pierre、Toupet, Loic

  DOI：——

  日期：——