2-benzyloxycarbonylamino-3-[3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid methyl ester | 89525-20-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-benzyloxycarbonylamino-3-[3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid methyl ester
• 英文别名: 1,3-bis<2-(benzyloxycarbonylamino)-2-(methoxycarbonyl)ethenyl>benzene；methyl (Z)-3-[3-[(Z)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)prop-1-enyl]phenyl]-2-(phenylmethoxycarbonylamino)prop-2-enoate
• CAS: 89525-20-2
• 化学式: C₃₀H₂₈N₂O₈
• 分子量: 544.561
• InChiKey: LCYJBGDAWZKXNX-MFYXSQMNSA-N

物化性质

• 沸点：
  717.8±60.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-benzyloxycarbonylamino-3-[3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid methyl ester 在 palladium on activated charcoal 、 Wilkinson's catalyst 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 168.0h， 生成 3-[3-(2-methoxycarbonyl-2-propionylamino-ethyl)-phenyl]-2-propionylamino-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition

  摘要：

  Acetylene derivatives of phenylalanine, phenethylamine and the multifunctional unnatural amino acids, phenyl-bis-alanine and phenyl-tris-alanine, were synthesized and functionalized with 2-azidoethyl beta-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranoside via regioselective copper(I)-mediated 1,3-dipolar cycloaddition to give a panel of mono-, di- and trivalent lactoside derivatives. Evaluation of the compounds as inhibitors against the tumour- and inflammation-related galectin-1, -3, 4N, 4C, -4, -7, -8N and -9N revealed a divalent compound with a K-d value as low as 3.2 mu M for galectin-1, which corresponded to a relative potency of 30 per lactose unit as compared to the natural disaccharide ligand lactose. This divalent compound had at least one order of magnitude higher affinity for galectin-1 than for any of the other galectins investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.028
• 作为产物：
  描述：

  methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate 在 sodium hydride 、 三氯化磷 作用下， 反应 22.0h， 生成 2-benzyloxycarbonylamino-3-[3-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Amino Acids and Peptides; XLIII¹. Dehydroamino Acids; XVIII². Synthesis of Dehydroamino Acids and Amino Acids fromN-Acyl-2-(dialkyloxyphosphinyl)-glycin Esters; II

  摘要：

  DOI：

  10.1055/s-1984-30730

文献信息

• Enantioselective Synthesis of Diamino Dicarboxylic Acids
  作者：Johann Hiebl、Hermann Kollmann、Franz Rovenszky、Karin Winkler

  DOI：10.1021/jo982034j

  日期：1999.3.1

  The preparation of alkyl diamino dicarboxylic acids with high optical purity (100% ee, >98.5% de) and high yields based on asymmetric catalytic hydrogenation is described. The required prochiral precursors are prepared from dialdehydes and Z-, Boc-, and acetyl-protected phosphonoglycines. Aqueous solutions of glyoxal, succinic dialdehyde, and glutaric dialdehyde were used to prepare the diunsaturated

  描述了基于不对称催化氢化制备具有高光学纯度（100％ee，＞ 98.5％de）和高产率的烷基二氨基二羧酸。所需的前手性前体由二醛和Z-，Boc-和乙酰基保护的膦酰甘氨酸制备。使用乙二醛，琥珀酸二醛和戊二醛的水溶液制备2,5-二氨基己二酸（DAA），2,7-二氨基丁二酸（DAS）和2,8-二氨基壬二酸（DAZ）的双不饱和前体。通过用[（COD）Rh（S，S）-Et-DuPHOS] OTf氢化相应的前手性原料，获得ZA保护的DAA，DAS和DAZ二甲基酯。
• Amino Acids and Peptides; XLIII¹. Dehydroamino Acids; XVIII². Synthesis of Dehydroamino Acids and Amino Acids from<i>N</i>-Acyl-2-(dialkyloxyphosphinyl)-glycin Esters; II
  作者：Ulrich Schmidt、Albrecht Lieberknecht、Jochen Wild

  DOI：10.1055/s-1984-30730

  日期：——
• Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition
  作者：Johan Tejler、Erik Tullberg、Torbjörn Frejd、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.carres.2006.04.028

  日期：2006.7

  Acetylene derivatives of phenylalanine, phenethylamine and the multifunctional unnatural amino acids, phenyl-bis-alanine and phenyl-tris-alanine, were synthesized and functionalized with 2-azidoethyl beta-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranoside via regioselective copper(I)-mediated 1,3-dipolar cycloaddition to give a panel of mono-, di- and trivalent lactoside derivatives. Evaluation of the compounds as inhibitors against the tumour- and inflammation-related galectin-1, -3, 4N, 4C, -4, -7, -8N and -9N revealed a divalent compound with a K-d value as low as 3.2 mu M for galectin-1, which corresponded to a relative potency of 30 per lactose unit as compared to the natural disaccharide ligand lactose. This divalent compound had at least one order of magnitude higher affinity for galectin-1 than for any of the other galectins investigated. (c) 2006 Elsevier Ltd. All rights reserved.