Z-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-NH2 | 865778-01-4

• 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: Z-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-NH2
• 英文别名: Cbz-D-Orn(Boc)(Boc)-D-Orn(Boc)(Boc)-D-Orn(Boc)(Boc)-D-Orn(Boc)(Boc)-D-Orn(Boc)(Boc)-D-Orn(Boc)(Boc)-D-Orn(Boc)(Boc)-D-Orn(Boc)(Boc)-NH2；tert-butyl N-[(4R)-5-amino-4-[[(2R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoyl]amino]pentanoyl]amino]pentanoyl]amino]pentanoyl]amino]pentanoyl]amino]pentanoyl]amino]-5-oxopentyl]carbamate
• CAS: 865778-01-4
• 化学式: C₈₈H₁₅₃N₁₇O₂₆
• 分子量: 1865.28
• InChiKey: ZZHAUOFBQAWSOZ-APHRHDSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  131
• 可旋转键数：
  67
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  592
• 氢给体数：
  17
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  Z-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-NH2 在 盐酸 、 三异丙基硅烷 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 生成 H-(D-Orn)8-NH2*nonahydrochloride 、 Z-D-Orn-D-Orn-D-Orn-D-Orn-D-Orn-D-Orn-D-Orn-D-Orn-NH2 octahydrochloride
  参考文献：
  名称：

  Concept and synthetic approach for a kilogram scale synthesis of octa-d-arginine amide nonahydrochloride salt

  摘要：

  Oligomers of arginine, such as octa-D-arginine amide, are excellent transporters for active drugs through cell membranes and tissue. The synthesis of octa-(D)-arginine amide, as the nonahydrochloride salt, was approached via a solution phase synthetic route involving the preparation of an octa-D-Ornithine intermediate, which was then converted into the desired octa-D-arginine compound through a guanidinylation step. The multi-step synthesis was carried out at pilot scale, resulting in the preparation of 700 g of the target molecule. No chromatographic purification was needed at any step of the process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.037
• 作为产物：
  描述：

  H-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-NH2 、 Z-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-OH 在 N-羟基-5-降冰片烯-2,3-二甲酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 Z-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-D-Orn(Boc)-NH2
  参考文献：
  名称：

  Concept and synthetic approach for a kilogram scale synthesis of octa-d-arginine amide nonahydrochloride salt

  摘要：

  Oligomers of arginine, such as octa-D-arginine amide, are excellent transporters for active drugs through cell membranes and tissue. The synthesis of octa-(D)-arginine amide, as the nonahydrochloride salt, was approached via a solution phase synthetic route involving the preparation of an octa-D-Ornithine intermediate, which was then converted into the desired octa-D-arginine compound through a guanidinylation step. The multi-step synthesis was carried out at pilot scale, resulting in the preparation of 700 g of the target molecule. No chromatographic purification was needed at any step of the process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.037