(1S,6R,7R,8S,10S,15R,16R,17S)-6,15-Dimethoxy-7,8,16,17-tetramethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione | 556811-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,6R,7R,8S,10S,15R,16R,17S)-6,15-Dimethoxy-7,8,16,17-tetramethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione
• 英文别名: (1S,6R,7R,8S,10S,15R,16R,17S)-6,15-dimethoxy-7,8,16,17-tetramethyl-4,9,13,18-tetraoxatricyclo[15.1.0.08,10]octadecane-3,12-dione
• CAS: 556811-53-1
• 化学式: C₂₀H₃₂O₈
• 分子量: 400.469
• InChiKey: XMRVFNQQPWISRQ-CILRADMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,6R,7R,8S,10S,15R,16R,17S)-6,15-Dimethoxy-7,8,16,17-tetramethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以91%的产率得到(3E,11E)-(5R,6R,7R,13R,14R,15R)-5,13-Dihydroxy-7,15-dimethoxy-5,6,13,14-tetramethyl-1,9-dioxa-cyclohexadeca-3,11-diene-2,10-dione
  参考文献：
  名称：

  Stereochemical Diversity through Cyclodimerization:  Synthesis of Polyketide-like Macrodiolides

  摘要：

  [GRAPHICS]An expeditious procedure for the direct formation of stereochemically well-defined macrodiolides is described. Cyclodimerizations of enantioenriched C7 and C8 hydroxy esters 6 in the presence of catalytic amounts of distannoxane transesterification catalysts afford 14- to 22-membered macrodiolides 7-9 bearing up to six stereocenters. Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11.

  DOI：

  10.1021/ol034608z
• 作为产物：
  描述：

  (E)-(5S,6R)-7-Hydroxy-6-methoxy-4,5-dimethyl-hept-3-enoic acid methyl ester 在 [Sn₂(C₄H₉)4SCN(OH)O]2 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 氯苯 为溶剂， 反应 52.0h， 生成 (1S,6R,7R,8S,10S,15R,16R,17S)-6,15-Dimethoxy-7,8,16,17-tetramethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione
  参考文献：
  名称：

  Stereochemical Diversity through Cyclodimerization:  Synthesis of Polyketide-like Macrodiolides

  摘要：

  [GRAPHICS]An expeditious procedure for the direct formation of stereochemically well-defined macrodiolides is described. Cyclodimerizations of enantioenriched C7 and C8 hydroxy esters 6 in the presence of catalytic amounts of distannoxane transesterification catalysts afford 14- to 22-membered macrodiolides 7-9 bearing up to six stereocenters. Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11.

  DOI：

  10.1021/ol034608z