(3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-7-(dimethyl(phenyl)silyl)heptane-2,6-dione | 1054666-78-2

• 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: (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-7-(dimethyl(phenyl)silyl)heptane-2,6-dione
• 英文别名: (3R,4S,5S)-1-[dimethyl(phenyl)silyl]-3,4,5,7-tetrakis(phenylmethoxy)heptane-2,6-dione
• CAS: 1054666-78-2
• 化学式: C₄₃H₄₆O₆Si
• 分子量: 686.92
• InChiKey: TVCKEAVOYDIVQA-PYHIYFCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-7-(dimethyl(phenyl)silyl)heptane-2,6-dione 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以80%的产率得到3,4,5,7-tetra-O-benzyl-1-deoxy-D-xylo-hepto-2,6-diulose
  参考文献：
  名称：

  1-Silyl-2,6-diketones:  Versatile Intermediates for the Divergent Synthesis of Five- and Six-Membered Carbocycles under Radical and Anionic Conditions

  摘要：

  1-Silyl-2,6-diketones, readily prepared by addition of (silylmethyl) metal reagents to 1,5-lactols followed by oxidation of the resultant diols, can be efficiently transformed into 3-hydroxycyclohexanones, cyclohex-2-enones, or 1-(silylmethyl)cyclopentane-1,2-diols under nucleophilic, basic, or single electron-transfer reduction conditions, respectively. The latter cyclitols can be further transformed into 2-methylenecyclopentanols or 1-(hydroxymethyl) cyclopentane-1,2-diols by Peterson elimination or Tamao-Fleming oxidation, respectively.

  DOI：

  10.1021/ol0613517
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 草酰氯 、 碘 、 magnesium 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-7-(dimethyl(phenyl)silyl)heptane-2,6-dione
  参考文献：
  名称：

  1-Silyl-2,6-diketones:  Versatile Intermediates for the Divergent Synthesis of Five- and Six-Membered Carbocycles under Radical and Anionic Conditions

  摘要：

  1-Silyl-2,6-diketones, readily prepared by addition of (silylmethyl) metal reagents to 1,5-lactols followed by oxidation of the resultant diols, can be efficiently transformed into 3-hydroxycyclohexanones, cyclohex-2-enones, or 1-(silylmethyl)cyclopentane-1,2-diols under nucleophilic, basic, or single electron-transfer reduction conditions, respectively. The latter cyclitols can be further transformed into 2-methylenecyclopentanols or 1-(hydroxymethyl) cyclopentane-1,2-diols by Peterson elimination or Tamao-Fleming oxidation, respectively.

  DOI：

  10.1021/ol0613517