[1S,2R,3R,4S,5R]-4-O-(4-bromophenylcarbamoyl)-1,2-epoxy-4,5,6-trihydroxy-5,6-O-isopropylidene-3-methyl-hexyl N,N-diisopropylcarbamate | 1245613-27-7

• 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: [1S,2R,3R,4S,5R]-4-O-(4-bromophenylcarbamoyl)-1,2-epoxy-4,5,6-trihydroxy-5,6-O-isopropylidene-3-methyl-hexyl N,N-diisopropylcarbamate
• 英文别名: [(2S,3R)-3-[(1S,2R)-1-[(4-bromophenyl)carbamoyloxy]-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]oxiran-2-yl] N,N-di(propan-2-yl)carbamate
• CAS: 1245613-27-7
• 化学式: C₂₄H₃₅BrN₂O₇
• 分子量: 543.455
• InChiKey: XTALVTITDVKMPV-GRARQNNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  98.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 [1S,2R,3R,4S,5R]-4-O-(4-bromophenylcarbamoyl)-1,2-epoxy-4,5,6-trihydroxy-5,6-O-isopropylidene-3-methyl-hexyl N,N-diisopropylcarbamate 在 potassium carbonate 作用下， 以54%的产率得到[4S,5S,5(1R,2S,2(4R))]-3-(4-bromophenyl)-4-[2-hydroxy-1-methyl-2,(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-5-methoxy-oxazolidin-2-one
  参考文献：
  名称：

  Highly stereoselective De-Novo synthesis of protected 2-amino-3-C-methyl-2,3-dideoxy-d-altrose

  摘要：

  A new strategy for the stereoselective synthesis of 2-amino-2-deoxy-aldoses is described. Therefore epoxy carbamates are reacted with isocyanates to furnish urethanes, which will form the title compounds with high diastereoselectivities under basic conditions and O,O-migration of the carbamoyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.101
• 作为产物：
  描述：

  (1S,2R,3R,4S,5R)-1,2-epoxy-4,5,6-trihydroxy-5,6-O-isopropylidene-3-methylhexyl N,N-diisopropylcarbamate 、 4-溴异氰酸苯酯 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以87%的产率得到[1S,2R,3R,4S,5R]-4-O-(4-bromophenylcarbamoyl)-1,2-epoxy-4,5,6-trihydroxy-5,6-O-isopropylidene-3-methyl-hexyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Highly stereoselective De-Novo synthesis of protected 2-amino-3-C-methyl-2,3-dideoxy-d-altrose

  摘要：

  A new strategy for the stereoselective synthesis of 2-amino-2-deoxy-aldoses is described. Therefore epoxy carbamates are reacted with isocyanates to furnish urethanes, which will form the title compounds with high diastereoselectivities under basic conditions and O,O-migration of the carbamoyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.101

文献信息

• Highly stereoselective De-Novo synthesis of protected 2-amino-3-C-methyl-2,3-dideoxy-d-altrose
  作者：Sabine Kollmann、Elisa Nauha、Dieter Hoppe

  DOI：10.1016/j.tet.2010.05.101

  日期：2010.8

  A new strategy for the stereoselective synthesis of 2-amino-2-deoxy-aldoses is described. Therefore epoxy carbamates are reacted with isocyanates to furnish urethanes, which will form the title compounds with high diastereoselectivities under basic conditions and O,O-migration of the carbamoyl group. (C) 2010 Elsevier Ltd. All rights reserved.