Benzyl 3-(benzyloxycarbonylamino)propyl di-N-isopropylphosphoramidite | 145471-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzyl 3-(benzyloxycarbonylamino)propyl di-N-isopropylphosphoramidite
• 英文别名: benzyloxy(3-benzyloxycarbonylaminopropoxy)(diisopropylamino)phosphine；benzyloxy N-(benzyloxycarbonyl)-3-amino-1-propoxy-N,N-diisopropylaminophosphite；(benzyloxy)<(3-N-carboxyamino)propyl>(diisopropylamino)phosphine；benzyloxy-(N-benzyloxycarbonyl-3-aminopropyloxy)-diisopropylamino phosphine；(benzyloxy)<(3-(N-carbobenzoxyamino)propyl)oxy>(diisopropylamino)phosphine；benzyloxy (N-benzyloxycarbonyl-3-amino-1-propyloxy)-N,N-diisopropylamino phosphine；benzyloxy-[(N-Cbz-3-amino-1-propyl)oxy](N,N-diisopropylamino)phosphine；benzyl N-[3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxypropyl]carbamate
• CAS: 145471-95-0
• 化学式: C₂₄H₃₅N₂O₄P
• 分子量: 446.527
• InChiKey: ZNVXNGGJBKUWDM-UHFFFAOYSA-N

物化性质

• 沸点：
  511.6±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl 3-(benzyloxycarbonylamino)propyl di-N-isopropylphosphoramidite 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 Benzyl (1,3,4,5,6-penta-O-allyl-myo-inosityl) 2-O-(N-Cbz-3-aminopropyl)phosphate
  参考文献：
  名称：

  Synthesis of tethered phytic acid

  摘要：

  The synthesis of 2-O-(3-aminopropyl) and 2-O-(6-aminohexyl)inositol hexakisphosphate provides two tetherable probes for isolation and characterization of IP6 and IP5 receptors.

  DOI：

  10.1016/s0040-4039(00)85982-1
• 作为产物：
  描述：

  氯甲酸苄酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 N,N-二异丙基乙胺 、 苯甲醇 作用下， 以 甲苯 为溶剂， 反应 70.0h， 生成 Benzyl 3-(benzyloxycarbonylamino)propyl di-N-isopropylphosphoramidite
  参考文献：
  名称：

  Syntheses of d-myo-inositol 1,4,5-trisphosphate affinity ligands

  摘要：

  A mixture of 2,3,6-tri-O-benzoyl-4,5-di-O-benzyl-D-myo-inositol and 1,3,6-tri-O-benzoyl-4,5-di-O-benzyl-D-myo-inositol, obtained during our synthesis of D-myo-inositol 1,4,5-trisphosphate [C.E. Ballou and W. Tegge, Proc. Natl. Acad. Sci. U.S.A., 86 (1989) 94-98], was separated after tetrahydropyranylation of the free hydroxyl group in each 2,3,6-Tri-O-benzoyl-4,5-di-O-benzyl-1-O-(tetrahydro-2-pyranyl)-D-myo-inositol was debenzylated and the two free hydroxyl groups were phosphorylated by a dinebzyl phosphoramidite procedure. The tetrahydropyranyl group was then removed, and phosphorylation at position 1 with benzyl 3-(benzyloxycarbonylamino)propyl di-N-isopropylphosphoramidite, followed by oxidation and deprotection, provided 1-[3-aminopropoxy(hydroxy)phosphinyl]-D-myo-inositol 4,5-bis-phosphate. This compound was coupled to activated agarose to prepare an affinity matrix for the isolation of D-myo-inositol 1,4,5-trisphosphate-binding proteins, and it was coupled to 4-azido-2-hydroxybenzoic acid to give a product that was labeled with I-125 to prepare a photoactivity derivatizing reagent. The new derivatives retain significant biological activity as assessed by their ability to stimulate the release of stored Ca2+ from the endoplasmic reticulum of permeabilized rat basophilic leukemia cells.

  DOI：

  10.1016/s0008-6215(00)90513-5

文献信息

• New tetherable derivatives of myo-inositol 2,4,5- and 1,3,4-trisphosphates
  作者：James F. Marecek、Virginia A. Estevez、Glenn D. Prestwich

  DOI：10.1016/0008-6215(92)85039-3

  日期：1992.10

  (+/-)-myo-Inositol 1-(3-aminopropyl hydrogen phosphate) 3,4-bis(disodium phosphate) (5) and (+/-)-myo-inositol 2-(3-aminopropyl hydrogen phosphate) 4,5-bis(disodium phosphate) (11) have been synthesized by conventional procedures. Each derivative has been immobilized on a polymeric resin in order to give a bioaffinity matrix.

  （+/-）-肌醇1-（3-氨基丙基磷酸氢）3,4-双（磷酸二钠）（5）和（+/-）-肌醇2-（3-氨基丙基磷酸氢）4通过常规方法合成了1-5-双（磷酸二钠）（11）。每种衍生物都已固定在聚合物树脂上，以提供生物亲和基质。
• Asymmetric Total Synthesis of <scp>d</scp>-<i>myo</i>-Inositol 1,2,4,5-Tetrakisphosphate and Its P-2-(<i>O</i>-Aminopropyl) Derivative
  作者：Jian Chen、György Dormán、Glenn D. Prestwich

  DOI：10.1021/jo951057k

  日期：1996.1.1
• Affinity probes for ins(1,3,4,5)P4 receptors
  作者：Virginia A. Estevez、Glenn D. Prestwich

  DOI：10.1016/s0040-4039(00)74288-2

  日期：1991.3

  A P-1-tethered derivative of Ins(1,3,4,5)P4 was synthesized and used to prepare a bioselective affinity matrix and a photoaffinity label for purification and covalent modification of IP4 receptor proteins.
• Synthesis of d-myo-P-1-(O-Aminopropyl)-Inositol-1,4,5-trisphosphate affinity probes from α-d-glucose
  作者：György Dormán、Jian Chen、Glenn D. Prestwich

  DOI：10.1016/0040-4039(95)01893-m

  日期：1995.11

  D-myo-P-1-(O-3-Aminopropyl)-Ins(1,4,5)P-3 has been synthesized from methyl alpha-D-glucopyranoside. This optically-pure tethered IP3 derivative has been converted to a selective photoaffinity label for modification of the ligand binding site of IP3 receptor proteins.
• Synthesis of P-5 tethered inositol-1,2,6-trisphosphate, an affinity reagent for α-trinositol receptors
  作者：Anu Chaudhary、György Dormán、Glenn D. Prestwich

  DOI：10.1016/s0040-4039(00)78333-x

  日期：1994.10

  The synthesis of D-myo-P-5-(O-aminopropyl)-Ins(1,2,5,6)P-4, a phosphodiester analog of Ins(1,2,6)P-3 tethered at the C-5 position, has been achieved and a photoaffinity label has been prepared.