((2S,3S,4R,6R)-6-((R)-1-(tert-butyldimethylsilyloxy)pent-4-ynyl)-2-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)tetrahydro-2H-pyran-3,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) | 1009360-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2S,3S,4R,6R)-6-((R)-1-(tert-butyldimethylsilyloxy)pent-4-ynyl)-2-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)tetrahydro-2H-pyran-3,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)
• 英文别名: [(2R,3S)-3-[(2S,3S,4R,6R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxypent-4-ynyl]oxan-2-yl]-1,4-dioxaspiro[4.4]nonan-2-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 1009360-02-4
• 化学式: C₅₂H₈₈O₇Si₄
• 分子量: 937.609
• InChiKey: HURXFCJYTIINQG-JABIJRJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.36
• 重原子数：
  63
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((2S,3S,4R,6R)-6-((R)-1-(tert-butyldimethylsilyloxy)pent-4-ynyl)-2-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)tetrahydro-2H-pyran-3,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) 在 Bu3SnAlEt2 、 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 以94%的产率得到((2S,3S,4R,6R)-6-((R)-1-(tert-butyldimethylsilyloxy)-4-iodopent-4-enyl)-2-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)tetrahydro-2H-pyran-3,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)
  参考文献：
  名称：

  Synthesis of the C(26)−C(42) and C(43)−C(67) Pyran-Containing Fragments of Amphidinol 3 via a Common Pyran Intermediate

  摘要：

  The pyran-containing fragments 1 and 2 of AM3 have been synthesized from the common pyran intermediate 3. Careful orchestration of the alcohol protecting groups was necessary to facilitate deprotection of alcohol functionality in the presence of the chemically sensitive polyene chain.

  DOI：

  10.1021/ol703042q
• 作为产物：
  描述：

  (R)-1-((2R,4R,5S,6S)-4,5-bis(tert-butyldimethylsilyloxy)-6-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)tetrahydro-2H-pyran-2-yl)pent-4-yn-1-ol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到((2S,3S,4R,6R)-6-((R)-1-(tert-butyldimethylsilyloxy)pent-4-ynyl)-2-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)tetrahydro-2H-pyran-3,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)
  参考文献：
  名称：

  Synthesis of the C(26)−C(42) and C(43)−C(67) Pyran-Containing Fragments of Amphidinol 3 via a Common Pyran Intermediate

  摘要：

  The pyran-containing fragments 1 and 2 of AM3 have been synthesized from the common pyran intermediate 3. Careful orchestration of the alcohol protecting groups was necessary to facilitate deprotection of alcohol functionality in the presence of the chemically sensitive polyene chain.

  DOI：

  10.1021/ol703042q