(3-methyloxetan-3-yl)methyl (2R)-{[(benzyloxy)-carbonyl]amino}(phenyl)acetate | 1101195-25-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3-methyloxetan-3-yl)methyl (2R)-{[(benzyloxy)-carbonyl]amino}(phenyl)acetate
• 英文别名: Cbz-Phg-Oxe；(3-methyloxetan-3-yl)methyl (2R)-2-phenyl-2-(phenylmethoxycarbonylamino)acetate
• CAS: 1101195-25-8
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: RGFVQIBHZTZHSJ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-methyloxetan-3-yl)methyl (2R)-{[(benzyloxy)-carbonyl]amino}(phenyl)acetate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到Cbz-D-Phg-OBO
  参考文献：
  名称：

  Nonracemizable Isocyanoacetates for Multicomponent Reactions

  摘要：

  Chiral ortho esters of a-isocyano acids were synthesized from commercially available Cbz-protected alpha-amino acids. These compounds are stable toward racemization in the Ugi 4CC in contrast to known esters of alpha-isocyano acids. Applying them in Ugi 4CC with subsequent deprotection gives access to dipeptides with preserved configuration at the C-terminal amino acid.

  DOI：

  10.1021/jo802420c
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 、 苄氧羰酰基苯甘氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3-methyloxetan-3-yl)methyl (2R)-{[(benzyloxy)-carbonyl]amino}(phenyl)acetate
  参考文献：
  名称：

  Nonracemizable Isocyanoacetates for Multicomponent Reactions

  摘要：

  Chiral ortho esters of a-isocyano acids were synthesized from commercially available Cbz-protected alpha-amino acids. These compounds are stable toward racemization in the Ugi 4CC in contrast to known esters of alpha-isocyano acids. Applying them in Ugi 4CC with subsequent deprotection gives access to dipeptides with preserved configuration at the C-terminal amino acid.

  DOI：

  10.1021/jo802420c

文献信息

• Nonracemizable Isocyanoacetates for Multicomponent Reactions
  作者：Alexander G. Zhdanko、Valentine G. Nenajdenko

  DOI：10.1021/jo802420c

  日期：2009.1.16

  Chiral ortho esters of a-isocyano acids were synthesized from commercially available Cbz-protected alpha-amino acids. These compounds are stable toward racemization in the Ugi 4CC in contrast to known esters of alpha-isocyano acids. Applying them in Ugi 4CC with subsequent deprotection gives access to dipeptides with preserved configuration at the C-terminal amino acid.