(3S,6RS)-6-[(2S)-2-((2S)-2-((2S)-2-(2-aminoacetamido)-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylic acid | 832111-48-5

• 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: (3S,6RS)-6-[(2S)-2-((2S)-2-((2S)-2-(2-aminoacetamido)-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylic acid
• 英文别名: (3S)-6-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-4-methylpentanoyl]amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]-3-methylbutanoyl]amino]-8-cyano-5-oxo-2,3,6,7-tetrahydro-1H-indolizine-3-carboxylic acid
• CAS: 832111-48-5
• 化学式: C₃₁H₄₇N₇O₉
• 分子量: 661.756
• InChiKey: VWBMYFZMNMMNIV-UJLIFSFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  250
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3S,6RS)-6-[(2S)-2-((2S)-2-((2S)-2-(2-aminoacetamido)-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylic acid 在 4-二甲氨基吡啶 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ((1S,7S,10S,13S)-18-Cyano-7-isobutyl-13-isopropyl-2,5,8,11,14,23-hexaoxo-3,6,9,12,15,22-hexaaza-tricyclo[14.5.2.0^19,22]tricos-18-en-10-yl)-acetic acid
  参考文献：
  名称：

  Synthesis of external β-turn templates by reaction of protected dehydroamino acids with cyclic enaminoesters

  摘要：

  Two external beta-turn templates have been synthesised and one of them has been derivatised as a GLDV-tetrapeptide. In the course of the synthesis an interesting dichotomy was observed in the condensation of exocyclic enamines such as 4 and 19 with protected dehydroamino acids using phosphorus trichloride. When dehydroamido acids were condensed with the enamines 4 and 19 then 6/6 and 6/5 fused bicyclic compounds such as 5 and 20, respectively, were obtained, whereas, when dehydroamino acid urethanes were used, the 5/6 and 5/5 fused products 7 and 23 were obtained. The bicyclic template 20 was converted to the GLDV-tetrapeptide derivative 31 but the sensitivity to base of the acyl-enamine system of the template reduced the yield in the synthesis of the external turn 35. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.036
• 作为产物：
  描述：

  ethyl (3S,6RS)-6-[(2S)-2-((2S)-2-((2S)-2-(2-aminoacetamido)-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以14%的产率得到(S)-5-[3-((S)-2-{(S)-2-[(S)-2-(2-Amino-acetylamino)-4-methyl-pentanoylamino]-3-tert-butoxycarbonyl-propionylamino}-3-methyl-butyrylamino)-3-carboxy-1-cyano-prop-(E)-ylidene]-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of external β-turn templates by reaction of protected dehydroamino acids with cyclic enaminoesters

  摘要：

  Two external beta-turn templates have been synthesised and one of them has been derivatised as a GLDV-tetrapeptide. In the course of the synthesis an interesting dichotomy was observed in the condensation of exocyclic enamines such as 4 and 19 with protected dehydroamino acids using phosphorus trichloride. When dehydroamido acids were condensed with the enamines 4 and 19 then 6/6 and 6/5 fused bicyclic compounds such as 5 and 20, respectively, were obtained, whereas, when dehydroamino acid urethanes were used, the 5/6 and 5/5 fused products 7 and 23 were obtained. The bicyclic template 20 was converted to the GLDV-tetrapeptide derivative 31 but the sensitivity to base of the acyl-enamine system of the template reduced the yield in the synthesis of the external turn 35. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.036