methyl 2-[(2R,3R,6S)-6-(hydroxymethyl)-3-(methoxymethoxy)-3,6-dihydro-2H-pyran-2-yl]acetate | 1164113-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2-[(2R,3R,6S)-6-(hydroxymethyl)-3-(methoxymethoxy)-3,6-dihydro-2H-pyran-2-yl]acetate
• CAS: 1164113-61-4
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: PIWHJOHAQUQYLD-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3R,6S)-6-(hydroxymethyl)-3-(methoxymethoxy)-3,6-dihydro-2H-pyran-2-yl]acetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以99%的产率得到
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Aspergillide B

  摘要：

  An efficient total synthesis of (+)-aspergillide B has been achieved, which features the C-glycosylation reaction for constructing the 2,6-trans-substituted pyran core, a highly effective four-step sequence without purification to produce the key intermediate 13 and an advantegous E-selective Julia-Kocienski olefination on a highly elaborate substrate. The synthesis confirmed the revised structure of aspergillide B by Uenishi.

  DOI：

  10.1021/jo900820f
• 作为产物：
  描述：

  methyl 2-[(2R,3R,6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(methoxymethoxy)-3,6-dihydro-2H-pyran-2-yl]acetate 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以85%的产率得到methyl 2-[(2R,3R,6S)-6-(hydroxymethyl)-3-(methoxymethoxy)-3,6-dihydro-2H-pyran-2-yl]acetate
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Aspergillide B

  摘要：

  An efficient total synthesis of (+)-aspergillide B has been achieved, which features the C-glycosylation reaction for constructing the 2,6-trans-substituted pyran core, a highly effective four-step sequence without purification to produce the key intermediate 13 and an advantegous E-selective Julia-Kocienski olefination on a highly elaborate substrate. The synthesis confirmed the revised structure of aspergillide B by Uenishi.

  DOI：

  10.1021/jo900820f

文献信息

• Concise Total Synthesis of (+)-Aspergillide B
  作者：Jian Liu、Ke Xu、Jinmei He、Ling Zhang、Xinfu Pan、Xuegong She

  DOI：10.1021/jo900820f

  日期：2009.7.17

  An efficient total synthesis of (+)-aspergillide B has been achieved, which features the C-glycosylation reaction for constructing the 2,6-trans-substituted pyran core, a highly effective four-step sequence without purification to produce the key intermediate 13 and an advantegous E-selective Julia-Kocienski olefination on a highly elaborate substrate. The synthesis confirmed the revised structure of aspergillide B by Uenishi.