(4R,5S,6R)-6-Benzyloxy-2-[(1S,3R,4S,5S,6R,7R,8R,9R)-5,7-bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-1-en-3-ol | 196860-53-4

• 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: (4R,5S,6R)-6-Benzyloxy-2-[(1S,3R,4S,5S,6R,7R,8R,9R)-5,7-bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-1-en-3-ol
• CAS: 196860-53-4
• 化学式: C₅₂H₇₈O₇Si₂
• 分子量: 871.358
• InChiKey: UUJXAKICBDJNPV-HNFYZTGOSA-N

物化性质

• 沸点：
  794.8±60.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.12
• 重原子数：
  61.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-6-Benzyloxy-2-[(1S,3R,4S,5S,6R,7R,8R,9R)-5,7-bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-1-en-3-ol 在 二硫化碳 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4R,4aS,5S,6R,7R,8R,8aR)-5,7-Bis-benzyloxy-4-[(E)-(3R,4S,5R)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-hex-1-enyl]-8-methoxymethoxy-6-methyl-octahydro-naphthalen-2-one
  参考文献：
  名称：

  Approach towards an EPC-synthesis of nodusmicin-IV. Construction of the highly hindered trisubstituted double bond of nodusmicin

  摘要：

  The highly substituted subunit 6 of our convergent synthesis of nodusmicin was prepared utilizing Evans' oxazolidinone protocol. Compound 6 was then adjoined to the decalin subunit 7 using Martin's olefination method. To improve on the formation of the hindered trisubstituted double bond, the following model reactions were devised: reductive coupling of ester and keto functionality of tricycle 16 led to the alpha-hydroxyketone, which was converted to the cyclic sulfate 19 via the diol. Sodium naphthalide then converted 19 to the olefins 20. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01521-9
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 、 锂硼氢 、 仲丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4R,5S,6R)-6-Benzyloxy-2-[(1S,3R,4S,5S,6R,7R,8R,9R)-5,7-bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-1-en-3-ol
  参考文献：
  名称：

  Approach towards an EPC-synthesis of nodusmicin-IV. Construction of the highly hindered trisubstituted double bond of nodusmicin

  摘要：

  The highly substituted subunit 6 of our convergent synthesis of nodusmicin was prepared utilizing Evans' oxazolidinone protocol. Compound 6 was then adjoined to the decalin subunit 7 using Martin's olefination method. To improve on the formation of the hindered trisubstituted double bond, the following model reactions were devised: reductive coupling of ester and keto functionality of tricycle 16 led to the alpha-hydroxyketone, which was converted to the cyclic sulfate 19 via the diol. Sodium naphthalide then converted 19 to the olefins 20. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01521-9