(S)-2-[(1R,2S,3R,5R,6S,7S)-5-((S)-2-Hydroxy-pentyl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-yl]-propionic acid methyl ester | 198822-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (S)-2-[(1R,2S,3R,5R,6S,7S)-5-((S)-2-Hydroxy-pentyl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-yl]-propionic acid methyl ester
• 英文别名: methyl (2S)-2-[(1R,2S,3R,5R,6S,7S)-5-[(2S)-2-hydroxypentyl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-yl]propanoate
• CAS: 198822-32-1
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: VGAXUPKBRJIAMO-YSHOZOJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[(1R,2S,3R,5R,6S,7S)-5-((S)-2-Hydroxy-pentyl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-yl]-propionic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 400.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 methyl (2S,3R,6S,8S)-3,6-epoxy-8-hydroxy-2-methylundecanoate
  参考文献：
  名称：

  A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

  摘要：

  The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00475-8
• 作为产物：
  描述：

  (Z)-3-[(1R,2S,3S,4S)-3-((1R,3S)-1,3-Dihydroxy-hexyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-2-methyl-acrylic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以93%的产率得到(S)-2-[(1R,2S,3R,5R,6S,7S)-5-((S)-2-Hydroxy-pentyl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-yl]-propionic acid methyl ester
  参考文献：
  名称：

  A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

  摘要：

  The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00475-8

文献信息

• A novel and efficient stereoselective synthesis of the southern part of pamamycin-607
  作者：Gérard Mandville、Christian Girard、Robert Bloch

  DOI：10.1016/s0957-4166(97)00475-8

  日期：1997.11

  The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.