(4S,5R)-2,2,5-trimethyl-3-(tert-butoxycarbonyl)-4-(Z-methoxycarbonylethenyl)-oxazolidine | 191013-79-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4S,5R)-2,2,5-trimethyl-3-(tert-butoxycarbonyl)-4-(Z-methoxycarbonylethenyl)-oxazolidine
• 英文别名: tert-butyl (4R,5R)-4-[(Z)-3-methoxy-3-oxoprop-1-enyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 191013-79-3
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: AYIVSUXAFDWOLW-DLXGREBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2,2,5-trimethyl-3-(tert-butoxycarbonyl)-4-(Z-methoxycarbonylethenyl)-oxazolidine 在 四氧化锇 、 二异丁基氢化铝 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 反应 144.08h， 生成 tert-butyl N-[(2R,3R,4R,5R)-4,5,6-trihydroxy-2-methyloxan-3-yl]carbamate
  参考文献：
  名称：

  A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxygulopyranoside and epi-tolyposamine

  摘要：

  New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00304-9
• 作为产物：
  描述：

  BOC-苏氨酸甲酯 在 18-冠醚-6 、 三氟化硼乙醚 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.41h， 生成 (4S,5R)-2,2,5-trimethyl-3-(tert-butoxycarbonyl)-4-(Z-methoxycarbonylethenyl)-oxazolidine
  参考文献：
  名称：

  A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxygulopyranoside and epi-tolyposamine

  摘要：

  New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00304-9

文献信息

• A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxygulopyranoside and epi-tolyposamine
  作者：Ari M.P. Koskinen、Leena A. Otsomaa

  DOI：10.1016/s0040-4020(97)00304-9

  日期：1997.5

  New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.