(1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-en-1-ol | 1001652-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-en-1-ol
• 英文别名: (Z,1S,5R)-5-[(2R,3S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,4-dioxaspiro[4.4]nonan-3-yl]-1-[(3R)-1,4-dioxaspiro[4.4]nonan-3-yl]-5-triethylsilyloxypent-3-en-1-ol
• CAS: 1001652-40-9
• 化学式: C₄₂H₆₄O₇Si₂
• 分子量: 737.137
• InChiKey: GMMOAHFDEYXKMH-ULRDGICJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-en-1-ol 、 甲基磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以90%的产率得到(1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-enyl methanesulfonate
  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：

  (1R,5S,Z)-1-((2R,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)pent-2-ene-1,5-diol 、 三乙基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到(1S,5R,Z)-5-((2S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-1-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-(triethylsilyloxy)pent-3-en-1-ol
  参考文献：
  名称：

  Concerning the Selective Protection of (Z)-1,5-syn-Ene-diols and (E)-1,5-anti-Ene-diols as Allylic Triethylsilyl Ethers

  摘要：

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.

  DOI：

  10.1021/ol702588h

文献信息

• Concerning the Selective Protection of (<i>Z</i>)-1,5-<i>syn</i>-Ene-diols and (<i>E</i>)-1,5-<i>anti</i>-Ene-diols as Allylic Triethylsilyl Ethers
  作者：Jacqueline D. Hicks、Chan Woo Huh、Ashley D. Legg、William R. Roush

  DOI：10.1021/ol702588h

  日期：2007.12.1

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.
• Synthesis of the C(26)−C(42) and C(43)−C(67) Pyran-Containing Fragments of Amphidinol 3 via a Common Pyran Intermediate
  作者：Jacqueline D. Hicks、William R. Roush

  DOI：10.1021/ol703042q

  日期：2008.2.1

  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.