1-deoxy-D-talonojirimycin*HCl | 473535-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-deoxy-D-talonojirimycin*HCl
• 英文别名: D-1-deoxy-talojirimycin hydrochloride；(2R,3S,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride；(2R,3S,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol;hydrochloride
• CAS: 473535-53-4
• 化学式: C₆H₁₃NO₄*ClH
• 分子量: 199.634
• InChiKey: ZJIHMALTJRDNQI-PVCLPBLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.99
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.5
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-O-tert-butyldimethylsilyl-1-deoxy-3,4-O-isopropylidene-D-talonojirimycin 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 1-deoxy-D-talonojirimycin*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

文献信息

• Synthesis of Eight 1-Deoxynojirimycin Isomers from a Single Chiral Cyanohydrin
  作者：Adrianus M. C. H. van den Nieuwendijk、Richard J. B. H. N. van den Berg、Mark Ruben、Martin D. Witte、Johannes Brussee、Rolf G. Boot、Gijsbert A. van der Marel、Johannes M. F. G. Aerts、Herman S. Overkleeft

  DOI：10.1002/ejoc.201200377

  日期：2012.6

  configurational 1-deoxynojirimycin isomers have been synthesized starting from a chiral cyanohydrin as the common precursor. The cyanohydrin chiral pool building block is easily accessible in large quantities by using almond hydroxynitrile lyase as the chiral catalyst in condensing hydrogen cyanide and crotonaldehyde. Our work complements the large body of literature on the synthesis of 1-deoxynojirimycin derivatives

  八种构型的 1-脱氧野尻霉素异构体已从手性氰醇作为常见前体合成。通过使用杏仁羟腈裂解酶作为缩合氰化氢和巴豆醛的手性催化剂，可以很容易地大量获得氰醇手性池结构单元。我们的工作补充了大量关于 1-脱氧野尻霉素衍生物合成的文献，其显着特征是这一类重要的糖苷酶抑制剂的八种立体异构体可以以有效的方式从一个常见的前体中衍生出来。
• Divergent synthesis of various iminocyclitols from <scp>d</scp>-ribose
  作者：Ramu Petakamsetty、Vipin Kumar Jain、Pankaj Kumar Majhi、Ramesh Ramapanicker

  DOI：10.1039/c5ob01042j

  日期：——

  A very efficient route to the diastereoselective synthesis of polyhydroxy pyrrolidines, piperidines and azepanes from an aldehyde derivative of ribose is reported.

  报道了一种从核糖醛衍生物开始，高度选择性地合成多羟基吡咯烷、哌啶和氮杂环庚烷的有效路线。
• 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.