1,5,6-trideoxy-1,5-imino-D-gluco-heptitol

• 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: 1,5,6-trideoxy-1,5-imino-D-gluco-heptitol
• 英文别名: (2R,3R,4R,5S)-2-(2-hydroxyethyl)piperidine-3,4,5-triol
• 化学式: C₇H₁₅NO₄
• 分子量: 177.2
• InChiKey: CJJRQVQPXAFTFW-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-O-[(t-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 platinum(IV) oxide 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium periodate 、 lithium aluminium tetrahydride 、 sodium azide 、 [(R)-BINAP]RuBr₂ 、 硫酸 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0~130.0 ℃ 、101.33 kPa 条件下， 反应 137.0h， 生成 1,5,6-trideoxy-1,5-imino-D-gluco-heptitol
  参考文献：
  名称：

  Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

  摘要：

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.022

文献信息

• Intermolecular Michael Addition of Substituted Amines to a Sugar-Derived α,β-Unsaturated Ester:  Synthesis of 1-Deoxy-<scp>d</scp>-<i>g</i><i>luco</i>- and -<scp>l</scp>-<i>i</i><i>do</i>-homonojirimycin, 1-Deoxy-castanospermine and 1-Deoxy-8a-<i>epi</i>-castanospermine
  作者：Nitin T. Patil、Jayant N. Tilekar、Dilip D. Dhavale

  DOI：10.1021/jo0010476

  日期：2001.2.1

  The synthesis of polyhydroxylated piperidine alkaloids, namely, 1-deoxy-D-gluco-homonojirimycin 3a, 1-deoxy-L-ido-homonojirimycin 3b, and indolizidine alkaloids 1-deoxy-castanospermine 5a and 1-deoxy-8a-epi-castanospermine 5b, has been achieved. The key step involved is the intermolecular Michael addition of benzylamine to alpha,beta-unsaturated ester 1, derived from D-glucose, which afforded diastereomeric

  多羟基化哌啶生物碱的合成，即1-脱氧-D-葡萄糖-homonojirimycin 3a，1-deoxy-L-ido-homonojirimycin 3b和吲哚并立生物碱1-deoxy-castanospermine 5a和1-deoxy-8a-ep-castanospermine 5b，已经实现。涉及的关键步骤是将分子胺在分子间的Michael加成反应中衍生自D-葡萄糖的α，β-不饱和酯1，从而得到β-氨基酯6a和6b的非对映异构体混合物，其中D-葡萄糖和L-ido-构型为C5分别。尝试增加和/或改变新生成的立体中心的非对映选择性。通过使用N-苄基氨基化锂作为迈克尔供体，在动力学控制的条件下实现了有利于L-偶合异构体6b的高立体选择性。β-氨基酯6a和6b代表目标分子的常见中间体。因此，LAH分别减少6a和6b，得到β-氨基醇7a和7b。依次氢解，氨基的选择性保护，然后水解1，2-丙酮化物
• Stereocontrolled 1,3-addition reaction of silyl ketene acetal to sugar nitrone: synthesis of d -gluco-homo-1-deoxynojirimycin and l -ido-homo-1-deoxynojirimycin
  作者：Nabendu N Saha、Vijaya N Desai、Dilip D Dhavale

  DOI：10.1016/s0040-4020(00)00981-9

  日期：2001.1

  The 1,3-addition reaction of silyl ketene acetal 6 to d-glucose derived nitrone 7 followed by reductive cleavage of the N–O bond afforded d-gluco- and l-ido-β-amino ester derivatives of 9a and 9b. The diastereoselectivity in addition reaction was improved as well as altered by making use of different Lewis acids. Reduction of the ester group in 9a followed by hydrogenolysis gave amino alcohol 12a.

  甲硅烷基乙烯酮缩醛6与d-葡萄糖衍生的硝酮7的1，3-加成反应，然后还原性切割N-O键，得到9a和9b的d-葡萄糖和L-氨基-β-氨基酯衍生物。通过使用不同的路易斯酸可以改善和改变加成反应中的非对映选择性。还原9a中的酯基，然后氢解得到氨基醇12a。选择性的N- Cbz保护，水解和分子内还原胺化作用提供了d-葡萄糖-homo-1-deoxynojirimycin 1d。类似地，β-氨基酯9b转化为l-ido -homo-1-deoxynojirimycin 1c。
• 2,3-diacylated, 2- and 3-mono-acylated alkylated imino sugars exhibiting glucosidase inhibition and their method of use
  申请人：Baruch S. Blumberg Institute

  公开号：US10421723B2

  公开（公告）日：2019-09-24

  Described herein are alkylated imino sugars derivatives having a disease-modifying action in the treatment of diseases associated with glucosidase activity that include viral hemorrhagic fevers and other enveloped viruses, and any other diseases involving glucosidase activity.

  本文描述的烷基化亚氨基糖衍生物在治疗与葡萄糖苷酶活性有关的疾病（包括病毒性出血热和其他包膜病毒）以及其他任何涉及葡萄糖苷酶活性的疾病方面具有疾病调节作用。
• Novel diacylated and mono-acylated alkylated imino sugars exhibiting glucosidase inhibition and their method of use
  申请人：Baruch S. Blumberg Institute

  公开号：US20170305856A1

  公开（公告）日：2017-10-26

  Described herein are alkylated imino sugars derivatives having a disease-modifying action in the treatment of diseases associated with glucosidase activity that include viral hemorrhagic fevers and other enveloped viruses, and any other diseases involving glucosidase activity.
• Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration
  作者：Géraldine Le Bouc、Christine Thomassigny、Christine Greck

  DOI：10.1016/j.tetasy.2006.07.022

  日期：2006.8

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.