(3S,4S)-4-methyl-5-methylene-4-[2-(trityloxy)ethyl]-3-[3-(trityloxy)propyl]dihydrofuran-2-one | 191034-86-3

• 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-methyl-5-methylene-4-[2-(trityloxy)ethyl]-3-[3-(trityloxy)propyl]dihydrofuran-2-one
• 英文别名: (3S,4S)-4-methyl-5-methylidene-4-(2-trityloxyethyl)-3-(3-trityloxypropyl)oxolan-2-one
• CAS: 191034-86-3
• 化学式: C₄₉H₄₆O₄
• 分子量: 698.902
• InChiKey: GMAYHLHSNPZVRT-MAHDSEGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 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-methyl-5-methylene-4-[2-(trityloxy)ethyl]-3-[3-(trityloxy)propyl]dihydrofuran-2-one 在 氨 作用下， 以 吡啶 、 乙醇 为溶剂， 110.0 ℃ 、106.66 Pa 条件下， 反应 37.0h， 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：

  (3S,4S)-5-hydroxy-4,5-dimethyl-4-(2-trityloxyethyl)-3-(3-trityloxypropyl)oxolan-2-one 在 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 生成 (3S,4S)-4-methyl-5-methylene-4-[2-(trityloxy)ethyl]-3-[3-(trityloxy)propyl]dihydrofuran-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.