benzyl 2-[(2R,6S)-6-[(2S)-3-[(1S,13R,14S,17S,21S,33R,34S,37S)-14,34-dimethyl-33-[(2S)-3-[(2S,6R)-6-(2-methyl-1-oxo-1-phenylmethoxypropan-2-yl)oxan-2-yl]-2-phenylmethoxypropyl]-11,31-dioxo-9,29-bis(phenylmethoxy)-12,32,41,42-tetraoxapentacyclo[35.3.1.117,21.05,10.025,30]dotetraconta-5(10),6,8,25(30),26,28-hexaen-13-yl]-2-phenylmethoxypropyl]oxan-2-yl]-2-methylpropanoate | 1325653-62-0

• 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: benzyl 2-[(2R,6S)-6-[(2S)-3-[(1S,13R,14S,17S,21S,33R,34S,37S)-14,34-dimethyl-33-[(2S)-3-[(2S,6R)-6-(2-methyl-1-oxo-1-phenylmethoxypropan-2-yl)oxan-2-yl]-2-phenylmethoxypropyl]-11,31-dioxo-9,29-bis(phenylmethoxy)-12,32,41,42-tetraoxapentacyclo[35.3.1.117,21.05,10.025,30]dotetraconta-5(10),6,8,25(30),26,28-hexaen-13-yl]-2-phenylmethoxypropyl]oxan-2-yl]-2-methylpropanoate
• CAS: 1325653-62-0
• 化学式: C₁₀₆H₁₃₂O₁₆
• 分子量: 1662.2
• InChiKey: HTWXPAHZLIXNJM-VHMRSJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.2
• 重原子数：
  122
• 可旋转键数：
  30
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  benzyl 2-[(2R,6S)-6-[(2S)-3-[(1S,13R,14S,17S,21S,33R,34S,37S)-14,34-dimethyl-33-[(2S)-3-[(2S,6R)-6-(2-methyl-1-oxo-1-phenylmethoxypropan-2-yl)oxan-2-yl]-2-phenylmethoxypropyl]-11,31-dioxo-9,29-bis(phenylmethoxy)-12,32,41,42-tetraoxapentacyclo[35.3.1.117,21.05,10.025,30]dotetraconta-5(10),6,8,25(30),26,28-hexaen-13-yl]-2-phenylmethoxypropyl]oxan-2-yl]-2-methylpropanoate 在 palladium 10% on activated carbon 、 氢气 、 盐酸 、 sodium chloride 作用下， 以 甲醇 、 正己烷 、 水 为溶剂， 反应 12.0h， 以70%的产率得到(+)-SCH 351448
  参考文献：
  名称：

  Total Synthesis of (+)-SCH 351448

  摘要：

  A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C-2-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide.

  DOI：

  10.1021/ol201863b
• 作为产物：
  描述：

  2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6R)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-hydroxy-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)benzoyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)benzoic acid 在 4-二甲氨基吡啶 、 2-chloro-1,3-dimethyl imidazolium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以60%的产率得到benzyl 2-[(2R,6S)-6-[(2S)-3-[(1S,13R,14S,17S,21S,33R,34S,37S)-14,34-dimethyl-33-[(2S)-3-[(2S,6R)-6-(2-methyl-1-oxo-1-phenylmethoxypropan-2-yl)oxan-2-yl]-2-phenylmethoxypropyl]-11,31-dioxo-9,29-bis(phenylmethoxy)-12,32,41,42-tetraoxapentacyclo[35.3.1.117,21.05,10.025,30]dotetraconta-5(10),6,8,25(30),26,28-hexaen-13-yl]-2-phenylmethoxypropyl]oxan-2-yl]-2-methylpropanoate
  参考文献：
  名称：

  Total Synthesis of (+)-SCH 351448

  摘要：

  A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C-2-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide.

  DOI：

  10.1021/ol201863b