(Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dien-1-ol | 343312-58-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dien-1-ol
• 英文别名: (2R,3S,4R,5Z)-2,3,4-tris(phenylmethoxy)octa-5,7-dien-1-ol
• CAS: 343312-58-3
• 化学式: C₂₉H₃₂O₄
• 分子量: 444.571
• InChiKey: XVVSUWQSHZHXRE-TVEAXOQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dien-1-ol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 0.5h， 以379 mg的产率得到(2R,3S,4R,Z)-1-acetoxy-2,3,4-tribenzyloxyocta-5,7-diene
  参考文献：
  名称：

  Synthesis of highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonanes from secondary sugar allyltin derivatives

  摘要：

  Secondary sugar allyltin derivatives of the D-series: Sug-CH(SnBu3)-CH=CH2 (obtained in an S(N)2' reaction of the corresponding primary allylic mesylates with 'Bu3SnCu') with the S-configuration at the stereogenic center bearing the -SnBu3 group decompose at 140degreesC to dienoaldehydes: CH2=CH-CH=CH-[(CHOR)(3)]-CHO with the cis geometry across the internal double bond. Such aldehydes react with the stabilized Wittig reagents to afford trienes, cyclization of which provides highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonenes. This methodology is complementary to that recently proposed by us leading to such bicyclic systems, but with the trans junction between the five- and six-membered rings. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00310-0
• 作为产物：
  描述：

  (Z)-(2S,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienal 在 sodium tetrahydroborate 作用下， 以70%的产率得到(Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dien-1-ol
  参考文献：
  名称：

  Stability of regioisomeric sugar allyltins. Cleavage of the carbon oxygen bond under radical conditions

  摘要：

  Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at high temperature (140 degreesC) with elimination of the tin moiety and opening of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH-CO2Me to afford the corresponding trienes, which spontaneously undergo stereoselective intramolecular [4+2] cycloaddition to optically pure, highly oxygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH=CHCH2-SnBu3] are thermally stable and do not decompose up to 170 degreesC. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00239-8

文献信息

• Stability of regioisomeric sugar allyltins. Cleavage of the carbon oxygen bond under radical conditions
  作者：Sławomir Jarosz、Katarzyna Szewczyk

  DOI：10.1016/s0040-4039(01)00239-8

  日期：2001.4

  Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at high temperature (140 degreesC) with elimination of the tin moiety and opening of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH-CO2Me to afford the corresponding trienes, which spontaneously undergo stereoselective intramolecular [4+2] cycloaddition to optically pure, highly oxygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH=CHCH2-SnBu3] are thermally stable and do not decompose up to 170 degreesC. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonanes from secondary sugar allyltin derivatives
  作者：Sławomir Jarosz、Katarzyna Szewczyk、Anna Zawisza

  DOI：10.1016/s0957-4166(03)00310-0

  日期：2003.6

  Secondary sugar allyltin derivatives of the D-series: Sug-CH(SnBu3)-CH=CH2 (obtained in an S(N)2' reaction of the corresponding primary allylic mesylates with 'Bu3SnCu') with the S-configuration at the stereogenic center bearing the -SnBu3 group decompose at 140degreesC to dienoaldehydes: CH2=CH-CH=CH-[(CHOR)(3)]-CHO with the cis geometry across the internal double bond. Such aldehydes react with the stabilized Wittig reagents to afford trienes, cyclization of which provides highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonenes. This methodology is complementary to that recently proposed by us leading to such bicyclic systems, but with the trans junction between the five- and six-membered rings. (C) 2003 Elsevier Science Ltd. All rights reserved.