(2S,4S)-1-{(2R,3S,6R,8R,9S)-8-[(1S,2S,3S)-1,2-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutyl]-9-methoxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-2-yl}-5-[(2S,6R)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]pentane-2,4-diol | 866021-55-8

• 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: (2S,4S)-1-{(2R,3S,6R,8R,9S)-8-[(1S,2S,3S)-1,2-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutyl]-9-methoxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-2-yl}-5-[(2S,6R)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]pentane-2,4-diol
• 英文别名: (1S,2S,3S)-1-[(2R,3S,6R,8R,9S)-8-[(2S,4S)-2,4-dihydroxy-5-[(2S,6R)-6-(2-hydroxyethyl)oxan-2-yl]pentyl]-3-methoxy-9-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-4-[(4-methoxyphenyl)methoxy]-3-methylbutane-1,2-diol
• CAS: 866021-55-8
• 化学式: C₃₆H₅₈O₁₁
• 分子量: 666.85
• InChiKey: MYBLEOQCYTXSCT-CXZCAJLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1-{(2R,3S,6R,8R,9S)-8-[(1S,2S,3S)-1,2-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutyl]-9-methoxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-2-yl}-5-[(2S,6R)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]pentane-2,4-diol 、 乙酸酐 在 吡啶 作用下， 以57%的产率得到acetic acid (1R,3S)-3-acetoxy-1-[(2S,6R)-6-(2-acetoxyethyl)tetrahydropyran-2-ylmethyl]-4-{(2R,3S,6R,8S,9S)-8-[(1S,2S,3S)-1,2-diacetoxy-4-(4-methoxybenzyloxy)-3-methylbutyl]-9-methoxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-2-yl}butyl ester
  参考文献：
  名称：

  Toward the Synthesis of Spirastrellolide A:  Construction of Two C₁−C₂₅ Diastereomers Containing the BC−Spiroacetal

  摘要：

  Stereocontrolled syntheses of two possible C-1-C-25 diastereomers of spirastrellolide A containing the cis-disubstituted tetrahydropyran and [6,6]-spiroacetal are reported, exploiting boron-mediated asymmetric aldol and allylation methodology.

  DOI：

  10.1021/ol051405x
• 作为产物：
  描述：

  (Z,1S,7S)-7-[(4R,6R)-6-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[(2S,6R)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]oxan-2-yl]propyl]-2,2-dimethyl-1,3-dioxan-4-yl]-1-[(4S,5R)-5-[(1S,2S)-1-[tert-butyl(dimethyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-methoxyoct-5-en-4-one 在 氢氟酸 、 水 作用下， 以 乙腈 为溶剂， 以55%的产率得到(2S,4S)-1-{(2R,3S,6R,8R,9S)-8-[(1S,2S,3S)-1,2-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutyl]-9-methoxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-2-yl}-5-[(2S,6R)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]pentane-2,4-diol
  参考文献：
  名称：

  Toward the Synthesis of Spirastrellolide A:  Construction of Two C₁−C₂₅ Diastereomers Containing the BC−Spiroacetal

  摘要：

  Stereocontrolled syntheses of two possible C-1-C-25 diastereomers of spirastrellolide A containing the cis-disubstituted tetrahydropyran and [6,6]-spiroacetal are reported, exploiting boron-mediated asymmetric aldol and allylation methodology.

  DOI：

  10.1021/ol051405x

文献信息

• Toward the Synthesis of Spirastrellolide A:  Construction of Two C₁−C₂₅ Diastereomers Containing the BC−Spiroacetal
  作者：Ian Paterson、Edward A. Anderson、Stephen M. Dalby、Olivier Loiseleur

  DOI：10.1021/ol051405x

  日期：2005.9.1

  Stereocontrolled syntheses of two possible C-1-C-25 diastereomers of spirastrellolide A containing the cis-disubstituted tetrahydropyran and [6,6]-spiroacetal are reported, exploiting boron-mediated asymmetric aldol and allylation methodology.