N-Boc-O-allyl-L-tyrosine amide N,N-di-Boc-amide | 147363-13-1

• 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: N-Boc-O-allyl-L-tyrosine amide N,N-di-Boc-amide
• 英文别名: N-Boc-O-Allyl-L-tyrosine N,N-di-Boc-amide；tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-prop-2-enoxyphenyl)propanoyl]carbamate
• CAS: 147363-13-1
• 化学式: C₂₇H₄₀N₂O₈
• 分子量: 520.623
• InChiKey: KKPNTLUBTODUNQ-FQEVSTJZSA-N

物化性质

• 密度：
  1.125±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-Boc-O-allyl-L-tyrosine amide N,N-di-Boc-amide 在 四丁基碘化铵 甲醇 、 sodium hexamethyldisilazane 、 potassium carbonate 、 乙酰氯 作用下， 反应 4.33h， 生成 methyl O-allyl-L-tyrosinate
  参考文献：
  名称：

  Practical synthesis of a highly enantioselective receptor for peptides

  摘要：

  A practical synthesis of a highly enantioselective, C3-symmetric host molecule (2) has been developed. The basic strategy is a significant improvement over the relatively lengthy previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)-benzoate to give an advanced intermediate (5). The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80% yield.

  DOI：

  10.1021/jo00058a005
• 作为产物：
  描述：

  L-酪氨酸甲酯盐酸盐 在 4-二甲氨基吡啶 、 氨 、 四丁基碘化铵 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 N-Boc-O-allyl-L-tyrosine amide N,N-di-Boc-amide
  参考文献：
  名称：

  Practical synthesis of a highly enantioselective receptor for peptides

  摘要：

  A practical synthesis of a highly enantioselective, C3-symmetric host molecule (2) has been developed. The basic strategy is a significant improvement over the relatively lengthy previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)-benzoate to give an advanced intermediate (5). The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80% yield.

  DOI：

  10.1021/jo00058a005

文献信息

• A.sub.4 B.sub.6 macrotricyclic enantioselective receptors for amino acid
  申请人：The Trustees of Columbia University in the City of New York

  公开号：US05599926A1

  公开（公告）日：1997-02-04

  The subject invention provides chiral receptor molecules having the structure: ##STR1## wherein A has the structure: ##STR2## and R.sub.1 and R.sub.2 are independently the same or different and are H, F, alkyl, aryl, etc.; X is CH.sub.2 or NH; Y is C.dbd.O or SO.sub.2 ; and n is 0 to about 3; which are useful for the purification of enantiomers of amino acid derivatives and other compounds. The subject invention also provides methods of preparing said receptor molecules.

  本发明提供了具有以下结构的手性受体分子：##STR1## 其中A具有以下结构：##STR2## R.sub.1和R.sub.2独立地相同或不同，可以是H，F，烷基，芳基等；X是CH.sub.2或NH；Y是C.dbd.O或SO.sub.2；n为0到约3；这些手性受体分子对氨基酸衍生物和其他化合物的对映体纯化非常有用。本发明还提供了制备所述受体分子的方法。
• Practical synthesis of a highly enantioselective receptor for peptides
  作者：Shawn D. Erickson、Julian A. Simon、W. Clark Still

  DOI：10.1021/jo00058a005

  日期：1993.3

  A practical synthesis of a highly enantioselective, C3-symmetric host molecule (2) has been developed. The basic strategy is a significant improvement over the relatively lengthy previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)-benzoate to give an advanced intermediate (5). The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80% yield.