(4aS,7S)-7-<2-(4-bromobenzoyloxy)ethyl>-1-(4-methoxy-2,3,6-trimethylbenzenesulfonylimino)-3-methyl-1,2,4a,5,6,7-hexahydropyrrolo<1,2-c>pyrimidine-4-carboxylic acid benzyl ester | 221493-47-6

• 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: (4aS,7S)-7-<2-(4-bromobenzoyloxy)ethyl>-1-(4-methoxy-2,3,6-trimethylbenzenesulfonylimino)-3-methyl-1,2,4a,5,6,7-hexahydropyrrolo<1,2-c>pyrimidine-4-carboxylic acid benzyl ester
• 英文别名: (4aS,7S)-7-[2-(4-Bromobenzoyloxy)ethyl]-l-(4-methoxy-2,3,6-trimethylbenzenesulfonylimino)-3-methyl-1,2,4a,5,6,7-hexahydropyrrolo[l,2-c]pyrimidine-4-carboxylic acid benzyl ester；benzyl (4aS,7S)-7-[2-(4-bromobenzoyl)oxyethyl]-1-(4-methoxy-2,3,6-trimethylphenyl)sulfonylimino-3-methyl-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-c]pyrimidine-4-carboxylate
• CAS: 221493-47-6
• 化学式: C₃₅H₃₈BrN₃O₇S
• 分子量: 724.673
• InChiKey: XSXHBZQGACYGCT-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4aS,7S)-7-<2-(4-bromobenzoyloxy)ethyl>-1-(4-methoxy-2,3,6-trimethylbenzenesulfonylimino)-3-methyl-1,2,4a,5,6,7-hexahydropyrrolo<1,2-c>pyrimidine-4-carboxylic acid benzyl ester 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4aS,7S)-1-(4-bromobenzoylimino)-7-<2-(4-bromobenzoyloxy)ethyl>-3-methyl-1,2,4a,5,6,7-hexahydropyrrolo<1,2-c>pyrimidine-4-carboxylic acid benzyl ester hydroformate
  参考文献：
  名称：

  Tuning Stereoselection in Tethered Biginelli Condensations. Synthesis of cis- or trans-1-Oxo- and 1-Iminohexahydropyrrolo[1,2-c]pyrimidines

  摘要：

  Stereoselection in tethered Biginelli condensations can be tuned to give either the cia or trans stereoisomer of 1-oxohexahydropyrrolo[1,2-c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).

  DOI：

  10.1021/jo981972g
• 作为产物：
  描述：

  4-溴苯甲酰氯 、 (S)-7-(2-Hydroxy-ethyl)-1-[(Z)-4-methoxy-2,3,6-trimethyl-benzenesulfonylimino]-3-methyl-1,2,4a,5,6,7-hexahydro-pyrrolo[1,2-c]pyrimidine-4-carboxylic acid benzyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4aR,7S)-7-<2-(4-bromobenzoyloxy)ethyl>-1-(4-methoxy-2,3,6-trimethylbenzenesulfonylimino)-3-methyl-1,2,4a,5,6,7-hexahydropyrrolo<1,2-c>pyrimidine-4-carboxylic acid benzyl ester 、 (4aS,7S)-7-<2-(4-bromobenzoyloxy)ethyl>-1-(4-methoxy-2,3,6-trimethylbenzenesulfonylimino)-3-methyl-1,2,4a,5,6,7-hexahydropyrrolo<1,2-c>pyrimidine-4-carboxylic acid benzyl ester 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Tuning Stereoselection in Tethered Biginelli Condensations. Synthesis of cis- or trans-1-Oxo- and 1-Iminohexahydropyrrolo[1,2-c]pyrimidines

  摘要：

  Stereoselection in tethered Biginelli condensations can be tuned to give either the cia or trans stereoisomer of 1-oxohexahydropyrrolo[1,2-c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).

  DOI：

  10.1021/jo981972g

文献信息

• Method for improved chemical synthesis of guanidinium alkaloids
  申请人：Overman E. Larry

  公开号：US20050239804A1

  公开（公告）日：2005-10-27

  Improved methods for convergent, total enantioselective synthesis of guanidinium alkaloid compounds including ones having cis- or -trans-1-oxo-and 1-iminohexahydropyrrolo [1,2c]pyrimidine units including, 13,14,15-isocrambescidin 800, crambescidin 800 and ptilomycalin A, for use as therapeutic agents having antifungal and/or antiviral and/or antitumor activity are provided. Methods for preparing novel pentacyclic intermediates for the preparation of the crambescidin/ptilomycalin family of guanidinium alkaloids and congeners are also disclosed.

  提供了改进的方法，用于收敛、完全对映选择性合成葫芦啶生物碱化合物，包括具有顺式或反式1-氧基和1-亚氨基六氢吡咯并[1,2c]嘧啶单元的化合物，包括13,14,15-异克林贝斯酸800、克林贝斯酸800和莫纳霉素A，用作具有抗真菌和/或抗病毒和/或抗肿瘤活性的治疗剂。还公开了制备新的五环中间体的方法，用于制备克林贝斯酸/莫纳霉素家族的葫芦啶生物碱及其同系物。