6-azido-6-deoxy-1,2;3,4-di-O-isopropylidene-β-D-ribohexulofuranose | 473442-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-1,2;3,4-di-O-isopropylidene-β-D-ribohexulofuranose
• 英文别名: (3'aR,4S,6'R,6'aR)-6'-(azidomethyl)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]
• CAS: 473442-25-0
• 化学式: C₁₂H₁₉N₃O₅
• 分子量: 285.3
• InChiKey: KITAXHMPMRGMJJ-HNBLOZHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-1,2;3,4-di-O-isopropylidene-β-D-ribohexulofuranose 在 palladium on activated charcoal 咪唑 、 三氟化硼乙醚 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.58h， 生成 6-O-tert-butyldimethylsilyl-1-deoxy-3,4-O-isopropylidene-D-talonojirimycin
  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：

  2,2,2',2'-四甲基四氢螺[1,3-二氧戊环-4,6'-[1,3]二氧杂环戊并[4,5-c]吡喃]-7'-醇 在 高氯酸 、 叠氮化锂 、 三乙胺 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 3.0h， 生成 6-azido-6-deoxy-1,2;3,4-di-O-isopropylidene-β-D-ribohexulofuranose
  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.