benzyl 2-((2R,6S)-6-((2S,4R,5S)-2-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-7-((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)-5-methylheptyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate | 864498-72-6

• 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,4R,5S)-2-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-7-((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)-5-methylheptyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate
• 英文别名: benzyl 2-[(2R,6S)-6-[(2S,4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-7-[(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]-5-methyl-2-phenylmethoxyheptyl]oxan-2-yl]-2-methylpropanoate
• CAS: 864498-72-6
• 化学式: C₅₅H₈₀O₉Si
• 分子量: 913.32
• InChiKey: YBAJBVSGUPQORY-XATPAIBMSA-N

物化性质

• 沸点：
  869.3±65.0 °C(predicted)
• 密度：
  1.063±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.11
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 2-((2R,6S)-6-((2S,4R,5S)-2-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-7-((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)-5-methylheptyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate 、 2-(trimethylsilyl)ethyl 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)benzoate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以63%的产率得到(2S,4R,5S)-2-(benzyloxy)-7-((2S,6S)-6-(3-(3-(benzyloxy)-2-((2-(trimethylsilyl)ethoxy)carbonyl)phenyl)propyl)tetrahydro-2H-pyran-2-yl)-1-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-5-methylheptan-4-yl 2-(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-((tert-butyldimethylsilyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)-6-hydroxybenzoate
  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：

  ((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)methyl acetate 在 Hoveyda-Grubbs catalyst second generation 、 草酰氯 、 sodium acetate 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 、 对甲苯磺酰肼 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 氯苯 为溶剂， 反应 38.0h， 生成 benzyl 2-((2R,6S)-6-((2S,4R,5S)-2-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-7-((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)-5-methylheptyl)tetrahydro-2H-pyran-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

文献信息

• Efficient Asymmetric Synthesis of (+)-SCH 351448
  作者：Sergei Bolshakov、James L. Leighton

  DOI：10.1021/ol0515006

  日期：2005.8.1

  An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allyisilylation reaction, which provides an efficient synthesis of 1,5-syn-diols.
• Total Synthesis of (+)-SCH 351448
  作者：Kaicheng Zhu、James S. Panek

  DOI：10.1021/ol201863b

  日期：2011.9.2

  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.