(3S,4S)-4-{[(tert-bytyldimethylsilyl)oxy]methyl}-3-methyl-7-(trityloxy)-3-[2-(trityloxy)ethyl]heptan-2-one | 191034-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3S,4S)-4-{[(tert-bytyldimethylsilyl)oxy]methyl}-3-methyl-7-(trityloxy)-3-[2-(trityloxy)ethyl]heptan-2-one
• 英文别名: (3S,4S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-7-trityloxy-3-(2-trityloxyethyl)heptan-2-one
• CAS: 191034-80-7
• 化学式: C₅₅H₆₄O₄Si
• 分子量: 817.196
• InChiKey: XNWQLJWDWGHFTL-CWKLFTOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.41
• 重原子数：
  60
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-{[(tert-bytyldimethylsilyl)oxy]methyl}-3-methyl-7-(trityloxy)-3-[2-(trityloxy)ethyl]heptan-2-one 在 重铬酸吡啶 、 四丁基氟化铵 、 氨 、 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 110.0 ℃ 、106.66 Pa 条件下， 反应 37.05h， 生成 (3S,4S)-4-methyl-5-methylene-4-[2-(trityloxy)ethyl]-3-[3-(trityloxy)propyl]pyrrolidin-2-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of a Nonracemic Vitamin B₁₂ A−B-Semicorrin

  摘要：

  The first synthesis of a vitamin B-12 A-B-semicorrin 44 is described. Both A and B rings were prepared from the same precursor, enamide 40, which is obtained by a sequence of sigmatropic rearrangements and a biomimetic oxylactonization. The coupling has been achieved via Eschenmoser sulfide contraction. A-B-semicorrin 44 allows a new approach toward vitamin B-12 and other uroporphinoids.

  DOI：

  10.1021/ja9700515
• 作为产物：
  描述：

  (4S,4(1S),5(S),5(1R)) and (4S,4(1S),5R,5(1S))-4-(1-{[(tert-bytyldimethylsilyl)oxy]methyl}-4-(trityloxy)butyl)-5-(1-hydroxyethyl)-4,5-dimethyldihydrofuran-2-one 在 lead(IV) acetate 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 48.08h， 生成 (3S,4S)-4-{[(tert-bytyldimethylsilyl)oxy]methyl}-3-methyl-7-(trityloxy)-3-[2-(trityloxy)ethyl]heptan-2-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of a Nonracemic Vitamin B₁₂ A−B-Semicorrin

  摘要：

  The first synthesis of a vitamin B-12 A-B-semicorrin 44 is described. Both A and B rings were prepared from the same precursor, enamide 40, which is obtained by a sequence of sigmatropic rearrangements and a biomimetic oxylactonization. The coupling has been achieved via Eschenmoser sulfide contraction. A-B-semicorrin 44 allows a new approach toward vitamin B-12 and other uroporphinoids.

  DOI：

  10.1021/ja9700515

文献信息

• Stereocontrolled Synthesis of a Nonracemic Vitamin B₁₂ A−B-Semicorrin
  作者：Johann Mulzer、Benjamin List、Jan W. Bats

  DOI：10.1021/ja9700515

  日期：1997.6.1

  The first synthesis of a vitamin B-12 A-B-semicorrin 44 is described. Both A and B rings were prepared from the same precursor, enamide 40, which is obtained by a sequence of sigmatropic rearrangements and a biomimetic oxylactonization. The coupling has been achieved via Eschenmoser sulfide contraction. A-B-semicorrin 44 allows a new approach toward vitamin B-12 and other uroporphinoids.