2-(2-hydroxyethoxy)ethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoate | 158573-53-6

• 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: 2-(2-hydroxyethoxy)ethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoate
• CAS: 158573-53-6
• 化学式: C₁₉H₂₉NO₇
• 分子量: 383.442
• InChiKey: NVGKMWHVHIHHBC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethoxy)ethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoate 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 4-二甲氨基吡啶 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 (9S,20S)-9,20-bis(hydroxymethyl)-1,4,7,13,16-pentaoxa-10,19-diazacyclohenicosane-8,11,18,21-tetrone
  参考文献：
  名称：

  Syntheses of Amino Acid Based Phosphodiester Linkage-Containing Cryptands as well as Diphosphorylated Macrocycles

  摘要：

  The synthesis of two amino acid based phosphodiester linkage-containing cryptands (30 and 44) as well as diphosphorylated macrocycles (28, 29, 32 and 33) are described. Boc-L-Ser(Bn)-OH and/or Boc-D-Ser(Bn)-OH were used for the construction of the construction of the precursors for the diphosphitylation and marcocyclization by phosphitylation. The carboxylic acid groups were connected with a diethylene glycol unit and the amino functionalities were linked using (ethylenedioxy)diacetic acid, oxydiacetic acid, or an isophthalic acid derivative. The LD-cryptands 30 and 44 were obtained after phosphitylation of the precursors 12 and 16, respectively, containing (ethylenedixoy)acetic acid or an isophthalic acid derivative as a bottom-spacer, using 4-chlorobenzyl phosphorodichlorodite followed by oxidation and hydrogenolysis. Phosphitylation of the precursors containing (ethylenedioxy)acetic acid or oxydiacetic acid as bottom-spacers 11-14, using bis(4-chlorobenzyl) N,N-diisopropylphosphoramidite and subsequent oxidation resulted in the corresponding diphosphorylated macrocycles 28, 29, 32, and 33.

  DOI：

  10.1021/jo00088a022
• 作为产物：
  描述：

  N-BOC-O-苄基-L-丝氨酸 、 二乙二醇 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， 以80%的产率得到2-(2-hydroxyethoxy)ethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoate
  参考文献：
  名称：

  氨基酸的含隐链的磷酸二酯键的合成。

  摘要：

  描述了基于氨基酸的含隐链的磷酸二酯键的合成。大环是使用Boc- L- Ser（OBn）-OH，Boc- D -Ser（OBn）-OH，二甘醇和乙二氧基二乙酸构造的。使用4-氯苄基二氯亚磷酸酯引入磷酸二酯键，从而形成穴状配体。

  DOI：

  10.1016/0040-4039(91)80575-q

文献信息

• Oijen Anita H. van, Huck Nina P. M., Kruijtzer John A. W., Erkelens Cees,+, J. Org. Chem, 59 (1994) N 9, S 2399-2408
  作者：Oijen Anita H. van, Huck Nina P. M., Kruijtzer John A. W., Erkelens Cees,+

  DOI：——

  日期：——
• Syntheses of Amino Acid Based Phosphodiester Linkage-Containing Cryptands as well as Diphosphorylated Macrocycles
  作者：Anita H. van Oijen、Nina P. M. Huck、John A. W. Kruijtzer、Cees Erkelens、Jacques H. van Boom、Rob M. J. Liskamp

  DOI：10.1021/jo00088a022

  日期：1994.5

  The synthesis of two amino acid based phosphodiester linkage-containing cryptands (30 and 44) as well as diphosphorylated macrocycles (28, 29, 32 and 33) are described. Boc-L-Ser(Bn)-OH and/or Boc-D-Ser(Bn)-OH were used for the construction of the construction of the precursors for the diphosphitylation and marcocyclization by phosphitylation. The carboxylic acid groups were connected with a diethylene glycol unit and the amino functionalities were linked using (ethylenedioxy)diacetic acid, oxydiacetic acid, or an isophthalic acid derivative. The LD-cryptands 30 and 44 were obtained after phosphitylation of the precursors 12 and 16, respectively, containing (ethylenedixoy)acetic acid or an isophthalic acid derivative as a bottom-spacer, using 4-chlorobenzyl phosphorodichlorodite followed by oxidation and hydrogenolysis. Phosphitylation of the precursors containing (ethylenedioxy)acetic acid or oxydiacetic acid as bottom-spacers 11-14, using bis(4-chlorobenzyl) N,N-diisopropylphosphoramidite and subsequent oxidation resulted in the corresponding diphosphorylated macrocycles 28, 29, 32, and 33.
• Synthesis of an amino acid based phosphodiester linkage containing cryptand.
  作者：A.H. van Oijen、H.B.A. de Bont、J.H. van Boom、R.M.J. Liskamp

  DOI：10.1016/0040-4039(91)80575-q

  日期：1991.12

  The synthesis of an amino acid based phosphodiester linkage containing cryptand is described. The macrocyclic ring is constructed using Boc-L-Ser(OBn)-OH, Boc-D-Ser(OBn)-OH, diethylene glycol and ethylene dioxydiacetic acid. The phosphodiester linkage was introduced employing 4-chlorobenzyl dichlorophosphite leading to the cryptand.

  描述了基于氨基酸的含隐链的磷酸二酯键的合成。大环是使用Boc- L- Ser（OBn）-OH，Boc- D -Ser（OBn）-OH，二甘醇和乙二氧基二乙酸构造的。使用4-氯苄基二氯亚磷酸酯引入磷酸二酯键，从而形成穴状配体。