1-deoxy-2,3;4,6-di-O-isopropylidene-L-gulonojirimycin | 792181-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-2,3;4,6-di-O-isopropylidene-L-gulonojirimycin
• 英文别名: (1R,2R,6R,9S)-4,4,12,12-tetramethyl-3,5,11,13-tetraoxa-8-azatricyclo[7.4.0.02,6]tridecane
• CAS: 792181-97-6
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: JWWXNKNMQJTFTO-SGIHWFKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-deoxy-2,3;4,6-di-O-isopropylidene-L-gulonojirimycin 在 盐酸 作用下， 反应 18.0h， 以90%的产率得到1-deoxy-L-gulonojirimycin*HCl
  参考文献：
  名称：

  Synthesis of 1-deoxy-l-gulonojirimycin (l-guloDNJ) and 1-deoxy-d-talonojirimycin (d-taloDNJ)

  摘要：

  Carbohydrate based syntheses of azasugars with unusual configurations viz. 1,5-dideoxy-1,5-imino-L-gulitol (L-gulo DNJ) and 1,5-dideoxy-1,5-imino-L-talitol (L-talo DNJ) are reported, from D-mannose and D-fructose, respectively. The key steps in both syntheses involved reductive aminative cyclizations. Thus, L-gulo DNJ was obtained by reduction of 2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannononitrile with LiAlH4 in DME to give the protected azasugar which upon hydrolysis with HCl afforded crystalline L-guloDNJ as the HCl salt in 29% overall yield. Reduction of 6-azido-1-O-tert-butyldimethylsityl-2,3-O-isopropylidene-beta-D-ribohexulofuranose obtained from D-fructose in six steps, followed by treatment with HCl, afforded L-talo DNJ as an HCl salt in similar to10% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00100-3
• 作为产物：
  描述：

  2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 4.0h， 以83%的产率得到1-deoxy-2,3;4,6-di-O-isopropylidene-L-gulonojirimycin
  参考文献：
  名称：

  Synthesis of 1-deoxy-l-gulonojirimycin (l-guloDNJ) and 1-deoxy-d-talonojirimycin (d-taloDNJ)

  摘要：

  Carbohydrate based syntheses of azasugars with unusual configurations viz. 1,5-dideoxy-1,5-imino-L-gulitol (L-gulo DNJ) and 1,5-dideoxy-1,5-imino-L-talitol (L-talo DNJ) are reported, from D-mannose and D-fructose, respectively. The key steps in both syntheses involved reductive aminative cyclizations. Thus, L-gulo DNJ was obtained by reduction of 2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannononitrile with LiAlH4 in DME to give the protected azasugar which upon hydrolysis with HCl afforded crystalline L-guloDNJ as the HCl salt in 29% overall yield. Reduction of 6-azido-1-O-tert-butyldimethylsityl-2,3-O-isopropylidene-beta-D-ribohexulofuranose obtained from D-fructose in six steps, followed by treatment with HCl, afforded L-talo DNJ as an HCl salt in similar to10% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00100-3

文献信息

• Synthesis of 1-deoxy-l-gulonojirimycin (l-guloDNJ) and 1-deoxy-d-talonojirimycin (d-taloDNJ)
  作者：Cosam C Joseph、Henk Regeling、Binne Zwanenburg、Gordon J.F Chittenden

  DOI：10.1016/s0008-6215(02)00100-3

  日期：2002.6

  Carbohydrate based syntheses of azasugars with unusual configurations viz. 1,5-dideoxy-1,5-imino-L-gulitol (L-gulo DNJ) and 1,5-dideoxy-1,5-imino-L-talitol (L-talo DNJ) are reported, from D-mannose and D-fructose, respectively. The key steps in both syntheses involved reductive aminative cyclizations. Thus, L-gulo DNJ was obtained by reduction of 2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannononitrile with LiAlH4 in DME to give the protected azasugar which upon hydrolysis with HCl afforded crystalline L-guloDNJ as the HCl salt in 29% overall yield. Reduction of 6-azido-1-O-tert-butyldimethylsityl-2,3-O-isopropylidene-beta-D-ribohexulofuranose obtained from D-fructose in six steps, followed by treatment with HCl, afforded L-talo DNJ as an HCl salt in similar to10% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.