methyl 4(S),5(S),6(R)-tri-O-benzyl-dec-2(E),7(E),9-trienoate | 849035-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4(S),5(S),6(R)-tri-O-benzyl-dec-2(E),7(E),9-trienoate
• 英文别名: methyl (2E,4S,5S,6R,7E)-4,5,6-tris(phenylmethoxy)deca-2,7,9-trienoate
• CAS: 849035-33-2
• 化学式: C₃₂H₃₄O₅
• 分子量: 498.619
• InChiKey: KGPKHRJLIKAOAN-RBVVROIBSA-N

物化性质

• 沸点：
  611.5±55.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4(S),5(S),6(R)-tri-O-benzyl-dec-2(E),7(E),9-trienoate 以 甲苯 、 苯 为溶剂， 20.0 ℃ 、999.99 MPa 条件下， 反应 24.0h， 以83%的产率得到(1R,2S,3S)-1,2,3-Tris-benzyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of complex carbobicyclic compounds from sugar allyltins: functionalization of the allylic position in bicyclo[4.3.0]nonene derivatives

  摘要：

  Two approaches for the fanctionalization of the allylic position in 7,8,9-tri-O-benzyl-5-substituted bicycio[4.3.0]non-2ene derivative 12 were examined. The first method, which involves an epoxidation of the C2-C3 double bond followed by a base induced isomerization, was found to be inappropriate. Although the epoxides were formed in good yields, the base-induced isomerization of the latter performed under the harsh conditions (LDA, HMPA, 80degreesC) did not lead to the desired allylic alcohol 13, but to the tricyclic derivative 15 resulting from the opening of the oxirane ring by the anion generated from the benzyl group at the C9-position. The other, more promising approach, consisted of the cis-hydroxylation of the C2-C3 double bond followed by selective protection of one of the hydroxyl groups (at the C2-position) using the dibutyltin methodology. The free hydroxyl group located at the C3 position can be eventually eliminated to give the desired olefin with the double bond between the C3 and C4 carbon atoms of the bicyclic system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.076
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6(E)-eno-α-D-gluco-oct-1,5-pyranoside 在 zinc(II) chloride 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 8.33h， 生成 methyl 4(S),5(S),6(R)-tri-O-benzyl-dec-2(E),7(E),9-trienoate
  参考文献：
  名称：

  Kozlowska, Elzbieta; Jarosz, Slawomir, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 889 - 898

  摘要：

  DOI：

文献信息

• Intramolecular Diels-Alder reaction of chiral, highly oxygenated trienoates derived from sugar allyltins
  作者：Slawomir Jarosz、Elżbieta Kozlowska、Artur Jeżewski

  DOI：10.1016/s0040-4020(97)00677-7

  日期：1997.8

  The Lewis acid catalyzed intramolecular Diels-Alder reaction of sugar derived trienoates 3 led preferably to bicyclic endo-adducts 4. The best stereoselectivity was observed for cyclization of the L-arabino-trienoate 3b, in which only one isomer (trans) was formed. High pressure (15 kbar) cycloaddition of 3a, 3b, and 3c, led to single stereoisomers 4a, 4b, and 4c in good yields. Conversion of adduct

  路易斯酸催化糖衍生的三烯酸酯3的分子内Diels-Alder反应优选导致双环内加合物4。对于L-阿拉伯糖三酸酯3b的环化，观察到最佳的立体选择性，其中仅形成一种异构体（反式）。3a，3b和3c的高压（15 kbar）环加成反应导致单立体异构体4a，4b和4c的产率很高。描述了加合物4a向手性环戊烷的转化。
• Kozlowska, Elzbieta; Jarosz, Slawomir, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 889 - 898
  作者：Kozlowska, Elzbieta、Jarosz, Slawomir

  DOI：——

  日期：——
• Synthesis of complex carbobicyclic compounds from sugar allyltins: functionalization of the allylic position in bicyclo[4.3.0]nonene derivatives
  作者：Sławomir Jarosz、Bartosz Boryczko、Piotr Cmoch、Ana M. Gomez、Cristobal Lopez

  DOI：10.1016/j.tetasy.2004.11.076

  日期：2005.1

  Two approaches for the fanctionalization of the allylic position in 7,8,9-tri-O-benzyl-5-substituted bicycio[4.3.0]non-2ene derivative 12 were examined. The first method, which involves an epoxidation of the C2-C3 double bond followed by a base induced isomerization, was found to be inappropriate. Although the epoxides were formed in good yields, the base-induced isomerization of the latter performed under the harsh conditions (LDA, HMPA, 80degreesC) did not lead to the desired allylic alcohol 13, but to the tricyclic derivative 15 resulting from the opening of the oxirane ring by the anion generated from the benzyl group at the C9-position. The other, more promising approach, consisted of the cis-hydroxylation of the C2-C3 double bond followed by selective protection of one of the hydroxyl groups (at the C2-position) using the dibutyltin methodology. The free hydroxyl group located at the C3 position can be eventually eliminated to give the desired olefin with the double bond between the C3 and C4 carbon atoms of the bicyclic system. (C) 2004 Elsevier Ltd. All rights reserved.