(S)-benzyl 2-t-butyloxycarbonylamino-2-methyl-4-pentenoate | 944086-92-4

• 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: (S)-benzyl 2-t-butyloxycarbonylamino-2-methyl-4-pentenoate
• 英文别名: benzyl (2S)-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoate
• CAS: 944086-92-4
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: YUGCUBGEHPOQTE-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-t-butyloxycarbonylamino-2-methyl-4-pentenoate 在 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 、 benzyl (4S,6R)-6-(iodomethyl)-4-methyl-2-oxo-1,3-oxazinane-4-carboxylate
  参考文献：
  名称：

  Stereoselective Iodocyclization of (S)-Allylalanine Derivatives:  γ-Lactone vs Cyclic Carbamate Formation

  摘要：

  An efficient procedure for highly chemo- and stereoselective cyclization of (S)-allylalanine derivatives is reported (diastereomeric ratios up to 96:4) where the reaction course can be completely controlled by switching from gamma-lactones to cyclic carbamates simply with the proper choice of the amino acid protecting groups. Both processes are stereoconvergent and afford the (S,S)-products in high yields, short reaction times, and mild reaction conditions.

  DOI：

  10.1021/ol070764k
• 作为产物：
  描述：

  (S)-(-)-α-烯丙基丙氨酸 在 sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 72.0h， 生成 (S)-benzyl 2-t-butyloxycarbonylamino-2-methyl-4-pentenoate
  参考文献：
  名称：

  Stereoselective Iodocyclization of (S)-Allylalanine Derivatives:  γ-Lactone vs Cyclic Carbamate Formation

  摘要：

  An efficient procedure for highly chemo- and stereoselective cyclization of (S)-allylalanine derivatives is reported (diastereomeric ratios up to 96:4) where the reaction course can be completely controlled by switching from gamma-lactones to cyclic carbamates simply with the proper choice of the amino acid protecting groups. Both processes are stereoconvergent and afford the (S,S)-products in high yields, short reaction times, and mild reaction conditions.

  DOI：

  10.1021/ol070764k

文献信息

• Stereoselective Iodocyclization of (<i>S</i>)-Allylalanine Derivatives:  γ-Lactone vs Cyclic Carbamate Formation
  作者：Mariella Pattarozzi、Cristiano Zonta、Quirinus B. Broxterman、Bernard Kaptein、Rita De Zorzi、Lucio Randaccio、Paolo Scrimin、Giulia Licini

  DOI：10.1021/ol070764k

  日期：2007.6.1

  An efficient procedure for highly chemo- and stereoselective cyclization of (S)-allylalanine derivatives is reported (diastereomeric ratios up to 96:4) where the reaction course can be completely controlled by switching from gamma-lactones to cyclic carbamates simply with the proper choice of the amino acid protecting groups. Both processes are stereoconvergent and afford the (S,S)-products in high yields, short reaction times, and mild reaction conditions.