Acetic acid (R)-2-acetoxy-1-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester | 122346-37-6

• 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 (R)-2-acetoxy-1-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester
• 英文别名: [(2R)-2-acetyloxy-2-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]ethyl] acetate
• CAS: 122346-37-6
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: MZJURPOWBADMCU-BZPMIXESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Acetic acid (1R,2S)-1-acetoxymethyl-2-hydroxy-2,6-dimethyl-hept-5-enyl ester 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 、 sodium acetate 、 溶剂黄146 作用下， 生成 Acetic acid (R)-2-acetoxy-1-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013

文献信息

• Stereoselective Synthesis of Tetrahydrofuran Moieties of Thyrsiferol and Venustatriol, Stereocontrolled Epoxidation of Bishomo- and Trishomo-allylic Alcohols
  作者：Koji Nozaki、Haruhisa Shirahama

  DOI：10.1246/cl.1988.1847

  日期：1988.11.5

  cis- and trans-2-(1,2-Diacetoxyethyl)-5-(1-hydroxy-1-methylethyl)-2-methyltetrahydrofurans were stereoselectively derived from 1,2-diacetoxy-3,7-dimethyloct-6-en-3-ol and 1,3-O-dimethoxybenzylidene-3,7-dimethyloct-6-en-2-ol respectively.

  cis-和trans-2-(1,2-二乙酸氧基乙基)-5-(1-羟基-1-甲基乙基)-2-甲基四氢呋喃分别是由1,2-二乙酸氧基-3,7-二甲基辛-6-烯-3-醇和1,3-O-二甲氧基苄叉-3,7-二甲基辛-6-烯-2-醇立体选择性衍生得到的。
• NOZAKI, KOJI;SHIRAHAMA, HARUHISA, CHEM. LETT.,(1988) N1, C. 1847-1848
  作者：NOZAKI, KOJI、SHIRAHAMA, HARUHISA

  DOI：——

  日期：——