(3S,4S)-5-hydroxy-4,5-dimethyl-4-(2-trityloxyethyl)-3-(3-trityloxypropyl)oxolan-2-one | 191034-82-9

• 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)-5-hydroxy-4,5-dimethyl-4-(2-trityloxyethyl)-3-(3-trityloxypropyl)oxolan-2-one
• CAS: 191034-82-9
• 化学式: C₄₉H₄₈O₅
• 分子量: 716.917
• InChiKey: LGOIXDATCWSVKF-APOWWDFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-5-hydroxy-4,5-dimethyl-4-(2-trityloxyethyl)-3-(3-trityloxypropyl)oxolan-2-one 在 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：

  (S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-4-trityloxy-butyl]-3,4-dimethyl-hexane-1,4,5-triol 在 lead(IV) acetate 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 四丁基氟化铵 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 48.08h， 生成 (3S,4S)-5-hydroxy-4,5-dimethyl-4-(2-trityloxyethyl)-3-(3-trityloxypropyl)oxolan-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.