(5S,15R)-21-heptoxy-5,15-bis(hydroxymethyl)-7,10,13-trioxa-4,16-diazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,14,17-tetrone | 158648-24-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: (5S,15R)-21-heptoxy-5,15-bis(hydroxymethyl)-7,10,13-trioxa-4,16-diazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,14,17-tetrone
• CAS: 158648-24-9
• 化学式: C₂₇H₄₀N₂O₁₀
• 分子量: 552.622
• InChiKey: FQYXFYFVLUKKLK-ZRZAMGCNSA-N

物化性质

• 沸点：
  935.3±65.0 °C(predicted)
• 密度：
  1.155±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (5S,15R)-21-heptoxy-5,15-bis(hydroxymethyl)-7,10,13-trioxa-4,16-diazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,14,17-tetrone 在 palladium on activated charcoal 氢气 、 sodium acetate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 sodium;(1R,13S)-7-heptoxy-25-oxido-25-oxo-15,18,21,24,26-pentaoxa-2,12-diaza-25λ5-phosphatricyclo[11.9.5.15,9]octacosa-5(28),6,8-triene-3,11,14,22-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：

  1,3-bis(cyanomethyl)-5-(heptyloxy)benzene 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， 25.0 ℃ 、405.3 kPa 条件下， 反应 10.17h， 生成 (5S,15R)-21-heptoxy-5,15-bis(hydroxymethyl)-7,10,13-trioxa-4,16-diazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,14,17-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

• 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.