2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol | 105615-44-9

• 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: 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol
• 英文别名: N-[(3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide
• CAS: 105615-44-9
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: GBRAQQUMMCVTAV-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl N-t-butyloxycarbonyl-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 在 palladium hydroxide - carbon 、 钯 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 氢气 、 三氟乙酸 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.75h， 生成 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol
  参考文献：
  名称：

  Synthesis of deoxymannojirimycin fagomine deoxynojirimycin 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol 2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol 2S,3R,4R,5R-trihydroxypipecolic acid and 2S,3R,4R,5S-trihydroxypipecolic acid from methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

  摘要：

  DOI：

  10.1016/s0040-4020(01)90035-3

文献信息

• 3-Amino-4,5-dihydroxypiperidines, process for their preparation and
  申请人：Bayer Aktiengesellschaft

  公开号：US04871747A1

  公开（公告）日：1989-10-03

  A 3-amino-4,5-dihydroxy-piperidine compound of the formula (I) ##STR1## in which R.sup.1 represents hydrogen, alkyl having up to 8 carbon atoms, aralkyl having 7 to 14 carbon atoms, or represents a group of the formula ##STR2## R.sup.4 denotes straight-chain or branched alkyl having up to 8 carbon atoms, straight-chain or branched alkoxy having up to 8 carbon atoms, or aralkoxy having up to 10 carbon atoms, and R.sup.2 and R.sup.3 represent hydrogen or represent the group NHR.sup.5, R.sup.5 having the same meaning as R.sup.1 and being identical to or different from the latter, with the proviso that, in every case, one substituent of R.sup.2 or R.sup.3 represents hydrogen and the other substituent of R.sup.2 or R.sup.3 represents NHR.sup.5, and physiologically acceptable salts thereof. Such compound is useful to treat prediabetes, gastritis, constipation, caries, atherosclerosis, obesity, diabetes and hyperlipoproteinaemia.

  化合物(I)是一种3-氨基-4,5-二羟基-哌啶化合物，其化学式为: ##STR1## 其中，R1代表氢、具有高达8个碳原子的烷基、具有7到14个碳原子的芳基烷基，或代表公式##STR2##的基团；R4代表直链或支链烷基，其具有高达8个碳原子，直链或支链烷氧基，其具有高达8个碳原子，或芳基烷氧基，其具有高达10个碳原子；R2和R3代表氢或代表基团NHR5，其中R5与R1具有相同的含义，并且与后者相同或不同，但必须保证，在每种情况下，R2或R3的一个取代基代表氢，而R2或R3的另一个取代基代表NHR5；以及其生理上可接受的盐。这种化合物可用于治疗糖尿病前期、胃炎、便秘、龋齿、动脉硬化、肥胖症、糖尿病和高脂蛋白血症。
• Synthesis of 2-Acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol and of 2-Acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol, a Potent and Specific Inhibitor of a Number of β-<i>N</i>-Acetylglucosaminidases
  作者：George W. J. Fleet、Paul W. Smith、Robert J. Nash、Linda E. Fellows、Raj B. Parekh、Thomas W. Rademacher

  DOI：10.1246/cl.1986.1051

  日期：1986.7.5

  The stereochemical outcome of the azide displacement of triflates derived from a piperidin-3-ol depends on the protecting group on the ring nitrogen and allows the synthesis of 2-acetamido-1,5-imino-1,2,5-trideoxy-d-glucitol (a potent and specific inhibitor of a number of β-N-acetylglucosaminidases) and of 2-acetamido-1,5-imino-1,2,5-trideoxy-d-mannitol.

  由哌啶-3-醇衍生的三氟酸盐的叠氮置换的立体化学结果取决于环氮上的保护基团，可以合成 2-乙酰氨基-1,5-亚氨基-1,2,5-三脱氧-d-葡萄糖醇（一种对多种 β-N-乙酰氨基葡萄糖苷酶有效的特异性抑制剂）和 2-乙酰氨基-1,5-亚氨基-1,2,5-三脱氧-d-甘露醇。
• Stereodivergent Syntheses of <i>altro</i> and <i>manno</i> Stereoisomers of 2-Acetamido-1,2-dideoxynojirimycin
  作者：Alex de la Fuente、Xavier Verdaguer、Antoni Riera

  DOI：10.1002/ejoc.201701282

  日期：2017.12.22

  The altro and manno isomers (8 and 9) of 2‐acetamido‐1,2‐dideoxynojirimycin have been synthesized from key intermediate 7. The key step was the stereoselective sulfite ring‐opening with retention of configuration due to the anchimeric effect of the endocyclic amine.

  2-乙酰氨基-2-1,2-二脱氧野oji霉素的altro和manno异构体（8和9）是从关键中间体7合成的。关键步骤是立体选择性亚硫酸盐开环，由于内环胺的嵌合效应，保留了构型。
• Treatment of energy utilization disease
  申请人：Vida Pharma Limited

  公开号：US10842784B2

  公开（公告）日：2020-11-24

  Described are compositions comprising imino sugar acids for the treatment of energy utilization disease (e.g. metabolic syndrome, including any disease or disorder associated therewith, for example central obesity, elevated levels of triglycerides and diabetes, including type 1 diabetes, type 2 diabetes and insulin resistance), processes for producing said compositions from various plant sources, together with various products, compounds, compositions, medical uses and methods based thereon.

  所描述的是包含亚氨基糖酸的组合物，用于治疗能量利用疾病（例如代谢综合征，包括与之相关的任何疾病或紊乱，例如中心性肥胖、甘油三酯水平升高和糖尿病，包括 1 型糖尿病、2 型糖尿病和胰岛素抵抗）；从各种植物来源生产所述组合物的工艺，以及基于此的各种产品、化合物、组合物、医疗用途和方法。
• Method for enhancing mutant enzyme activities in gaucher disease
  申请人：Fan Jian-Qiang

  公开号：US20050113415A1

  公开（公告）日：2005-05-26

  Method for enhancing in a mammalian cell the activity of an enzyme associated with Gaucher Disease by administering a competitive inhibitor of glucocerebrosidase in an amount effective to enhance the activity of the enzyme. Preferred compounds for use in the method are imino sugars and related compounds. In particular, C8-12-alkyl derivatives of N-alkyl-deoxynojirimycin, isofagomine compounds, and calystegine compounds are effective to enhance glucocerebrosidase activity.

  提高哺乳动物细胞中与戈谢病有关的酶的活性的方法，方法是施用有效量的葡萄糖脑苷脂酶竞争性抑制剂，以提高该酶的活性。用于该方法的优选化合物是亚氨基糖和相关化合物。特别是，N-烷基-脱氧野尻霉素的C8-12-烷基衍生物、异法戈明化合物和卡尔斯泰金化合物可有效增强葡萄糖脑苷脂酶的活性。