(11aR)-10-N-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (11aR)-10-N-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione
• 英文别名: (6aR)-5-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl]-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepine-6,11-dione
• 化学式: C₂₄H₃₀N₂O₇
• 分子量: 458.511
• InChiKey: BAVWJQBDTJJYRV-YNBFPDEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (11aR)-10-N-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (11aR)-10-N-(6-deoxy-α-D-galactopyranos-6-yl)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione 、 (11aR)-10-N-(6-deoxy-β-D-galactopyranos-6-yl)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione
  参考文献：
  名称：

  Synthesis and epimerization of 10-N-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranos-6-yl)-(11aS)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione

  摘要：

  The reaction of the 1.,2:3,4-di-O-isopropylidene-6-O-tosyl-alpha -D-galactopyranose 2 with (11aS)-pyrrolo[2,1-c][1,4]benzodiazepin-5.11-dione 1. prepared front L-proline and isatoic anhydride, gave two products which were previously reported as conformational isomers. In this work. an X-ray crystallographic study showed these to be the diastereomeric pair (HaS)- and (11aR)-10-N-(6-deoxy-1.2:3.4-di-O-isopropylidene-alpha -D-galactropyranos-6-yl)-pyrrolo[2,1-c,][1,4]benzodiazepin-5.11-diones as a consequence of C(11a) epimerization in the benzodiazepine moiety during glycosylation under basic reaction conditions, The hydrosolubility of the deprotected products ere compared with those of the analogous benzodiazepine derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00282-8
• 作为产物：
  描述：

  (S)-(+)-2,3-二氢-1H-吡咯并[2,1-c][1,4]苯并二氮卓-5,11(10H,11aH)-二酮 、 1,2:3,4-二-o-异亚丙基-6-o-对甲苯磺酰基-alpha-D-半乳糖 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以39%的产率得到(11aR)-10-N-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione
  参考文献：
  名称：

  Synthesis and epimerization of 10-N-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranos-6-yl)-(11aS)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione

  摘要：

  The reaction of the 1.,2:3,4-di-O-isopropylidene-6-O-tosyl-alpha -D-galactopyranose 2 with (11aS)-pyrrolo[2,1-c][1,4]benzodiazepin-5.11-dione 1. prepared front L-proline and isatoic anhydride, gave two products which were previously reported as conformational isomers. In this work. an X-ray crystallographic study showed these to be the diastereomeric pair (HaS)- and (11aR)-10-N-(6-deoxy-1.2:3.4-di-O-isopropylidene-alpha -D-galactropyranos-6-yl)-pyrrolo[2,1-c,][1,4]benzodiazepin-5.11-diones as a consequence of C(11a) epimerization in the benzodiazepine moiety during glycosylation under basic reaction conditions, The hydrosolubility of the deprotected products ere compared with those of the analogous benzodiazepine derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00282-8

文献信息

• Synthesis and epimerization of 10-N-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranos-6-yl)-(11aS)-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione
  作者：Driss Bouhlal、Patrick Martin、Mohamed Massoui、Guy Nowogrocki、Serge Pilard、Pierre Villa、Gérard Goethals

  DOI：10.1016/s0957-4166(01)00282-8

  日期：2001.7

  The reaction of the 1.,2:3,4-di-O-isopropylidene-6-O-tosyl-alpha -D-galactopyranose 2 with (11aS)-pyrrolo[2,1-c][1,4]benzodiazepin-5.11-dione 1. prepared front L-proline and isatoic anhydride, gave two products which were previously reported as conformational isomers. In this work. an X-ray crystallographic study showed these to be the diastereomeric pair (HaS)- and (11aR)-10-N-(6-deoxy-1.2:3.4-di-O-isopropylidene-alpha -D-galactropyranos-6-yl)-pyrrolo[2,1-c,][1,4]benzodiazepin-5.11-diones as a consequence of C(11a) epimerization in the benzodiazepine moiety during glycosylation under basic reaction conditions, The hydrosolubility of the deprotected products ere compared with those of the analogous benzodiazepine derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.