(9S,20S)-9,20-bis(hydroxymethyl)-1,4,7,13,16-pentaoxa-10,19-diazacyclohenicosane-8,11,18,21-tetrone | 139338-70-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (9S,20S)-9,20-bis(hydroxymethyl)-1,4,7,13,16-pentaoxa-10,19-diazacyclohenicosane-8,11,18,21-tetrone
• CAS: 139338-70-8
• 化学式: C₁₆H₂₆N₂O₁₁
• 分子量: 422.389
• InChiKey: JRRFTLWGMZDBPV-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  179
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (9S,20S)-9,20-bis(hydroxymethyl)-1,4,7,13,16-pentaoxa-10,19-diazacyclohenicosane-8,11,18,21-tetrone 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 bis[(4-chlorophenyl)methyl] [(9S,20S)-20-(hydroxymethyl)-8,11,18,21-tetraoxo-1,4,7,13,16-pentaoxa-10,19-diazacyclohenicos-9-yl]methyl phosphate
  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：

  三乙二醇 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 甲醇 为溶剂， 反应 2.17h， 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

文献信息

• 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。
• 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：——