2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannonitrile | 473442-23-8

• 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: 2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannonitrile
• 英文别名: [(4S,5R)-4-[(4R,5R)-5-cyano-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxan-5-yl] 4-methylbenzenesulfonate
• CAS: 473442-23-8
• 化学式: C₁₉H₂₅NO₇S
• 分子量: 411.476
• InChiKey: SJUZGUXBDMWMFA-QBPKDAKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannonitrile 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 22.0h， 生成 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：

  在 palladium on activated charcoal 吡啶 、 草酰氯 、 氨 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 5.0~20.0 ℃ 、101.33 kPa 条件下， 反应 168.5h， 生成 2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannonitrile
  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