8-benzyl 4-ethyl (7RS)-7-benzyloxycarbonylamino-6,7-dihydro-3,7-dimethyl-6-oxo-2H-pyrrolo[2,1-b][1,3]thiazine-4,8-dicarboxylate

• 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: 8-benzyl 4-ethyl (7RS)-7-benzyloxycarbonylamino-6,7-dihydro-3,7-dimethyl-6-oxo-2H-pyrrolo[2,1-b][1,3]thiazine-4,8-dicarboxylate
• 英文别名: 8-O-benzyl 4-O-ethyl 3,7-dimethyl-6-oxo-7-(phenylmethoxycarbonylamino)-2H-pyrrolo[2,1-b][1,3]thiazine-4,8-dicarboxylate
• 化学式: C₂₈H₂₈N₂O₇S
• 分子量: 536.606
• InChiKey: AGABNURHLQLALV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Z-脱氢丙氨酸 、 ethyl 2-benzyloxycarbonylmethylene-3,6-dihydro-5-methyl-2H-[1,3]-thiazine-4-carboxylate 在 三氯化磷 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 5.0h， 以57%的产率得到8-benzyl 4-ethyl (7RS)-7-benzyloxycarbonylamino-6,7-dihydro-3,7-dimethyl-6-oxo-2H-pyrrolo[2,1-b][1,3]thiazine-4,8-dicarboxylate
  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