(2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid | 108428-44-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid
• 英文别名: (1R,4R,4R,5S)-3,4,5-trihydroxypipecolic acid；2R,3R,4R,5S-3,4,5-Trihydroxypipecolic acid；2R,3R,4R,5S-trihydroxypipecolic acid；L-idurono-deoxynojirimycin；(2R,3R,4R,5S)-trihydroxypipecolic acid；1-deoxy-5-aza-L-idopyranuronic acid
• CAS: 108428-44-0
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: ZHFMVVUVCALAMY-NRXMZTRTSA-N

物化性质

• 沸点：
  442.1±45.0 °C(Predicted)
• 密度：
  1.676±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid 生成 methyl (2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylate
  参考文献：
  名称：

  LOCKHOFF, OSWALD;HAYAUCHI, YUTAKA

  摘要：

  DOI：
• 作为产物：
  描述：

  D-glucurono-3,6-lactone acetonide 在 钯 sodium azide 、 氢气 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.5h， 生成 (2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid
  参考文献：
  名称：

  由葡糖醛酸内酯合成多羟基化氨基酸：2s，3r，4r，5s-三羟基哌酸，2r，3r，4r，5s-三羟基哌酸和2r，3r，4r-二羟基脯氨酸的对映体合成

  摘要：

  2S，3R，4R，5S-三羟基-哌酸，2R，3R，4R，5S-三羟基哌酸和2R，3R，4R-的对映体特异性合成说明了D-葡糖醛酸内酯合成多羟基氨基酸的潜力。二羟脯氨酸。

  DOI：

  10.1016/s0040-4020(01)89972-5

文献信息

• Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases
  作者：Yuichi Yoshimura、Chiaki Ohara、Tatsushi Imahori、Yukako Saito、Atsushi Kato、Saori Miyauchi、Isao Adachi、Hiroki Takahata

  DOI：10.1016/j.bmc.2008.06.016

  日期：2008.9

  kinetic resolution, the synthesis of both L- and D-isomers of 3,4,5-trihydroxy- and 3-hydroxypipecolic acids was achieved. None of the compounds tested showed inhibitory activity against alpha- and beta-glucosidases. On the other hand, L-23 and L-29 were found to have potent inhibitory activity against beta-glucuronidase. In addition, it is interesting that some uronic-type azasugar derivatives showed moderate

  我们已经合成了对应于糖醛酸的5-氮杂衍生物的3-羟基-和3,4,5-三羟基哌酸衍生物，并评估了它们对包括β-葡萄糖醛酸苷酶在内的各种糖苷酶的抑制活性。选择化合物4和5作为合成3,4,5-三羟基哌酸和3-羟基哌酸以及3-羟基贝白蛋白（从有毒蘑菇中分离出的独特天然产物）的常用中间体。N-Boc-烯丙基甘氨酸衍生物与丙烯醛的交叉羟醛缩合反应，然后进行闭环易位，得到非对映异构体混合物的4和5，可以通过硅胶柱色谱法分离。通过使用脂肪酶催化的动力学拆分，可以合成3,4,5-三羟基和3-羟基哌酸的L-异构体和D-异构体。所测试的化合物均未显示出对α-和β-葡糖苷酶的抑制活性。另一方面，发现L-23和L-29对β-葡糖醛酸糖苷酶具有有效的抑制活性。另外，有趣的是，一些糖醛酸型的氮杂糖衍生物显示出对β-N-乙酰氨基葡糖苷酶的中等抑制活性。
• A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline, 1,4-Dideoxy-1,4-imino-l-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-l-iditol
  作者：Byong Won Lee、Ill-Yun Jeong、Min Suk Yang、Sang Uk Choi、Ki Hun Park

  DOI：10.1055/s-2000-6408

  日期：——

  The syntheses of pyrrolidine alkaloids (-)-1 and (+)-3 were accomplished in 47% and 60% overall yield from 2-azido-2-deoxy-l-idonate 5, while piperidine alkaloids (-)-2 and (+)-4 were obtained in 51% and 53% overall yield from the same starting material. Key step includes iodine promoted one-pot cyclization, and selective deprotection of isopropylidene and 9-phenylfluoren-9-yl (Pf) group.

  从 2-azido-2-deoxy-l-idonate 5 合成吡咯烷生物碱 (-)-1 和 (+)-3 的总收率分别为 47% 和 60%，而从相同的起始原料合成哌啶生物碱 (-)-2 和 (+)-4 的总收率分别为 51% 和 53%。关键步骤包括碘促进的一锅环化，以及异亚丙基和 9-苯基芴-9-基 (Pf) 基团的选择性脱保护。
• Synthesis of chiral pyrrolidine and piperidine glycosidase inhibitors
  申请人：MONSANTO COMPANY

  公开号：EP0439444A2

  公开（公告）日：1991-07-31

  There is disclosed a novel method for the syntheses of chiral pyrrolidines and piperidines by the intramolecular ring closure of anomeric mixtures of 4-amino- and 5-amino-2-trifluoromethanesulfonates of methyl furanosides. The novel method preferably provides for the efficient syntheses from diacetone glucose of 1,4-dideoxy-1,4-imino-D-arabinitol - known as DAB1, (2S,3R,4R)-3,4-dihydroxyproline, fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol], and (2S,3R,4R)-3,4-dihydroxypipecolic acid by intramolecular nucleophilic displacement by an amino function of 2-O-trifluoromethanesulphonates of anomeric mixtures of methyl furanosides.

  本发明公开了一种通过甲基呋喃糖苷的 4-氨基和 5-氨基-2-三氟甲磺酸异构体混合物的分子内环闭合合成手性吡咯烷和哌啶的新方法。这种新方法可以从二丙酮葡萄糖中高效合成 1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇（又称 DAB1）、(2S,3R,4R)-3,4-二羟基脯氨酸、法戈明[1,5-亚氨基-1,2、和(2S,3R,4R)-3,4-二羟基哌啶酸的分子内亲核置换。
• 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。
• Synthesis of glycosaminoglycan oligosaccharides. Part 4: Synthesis of aza-l-iduronic acid-containing analogs of heparan sulfate oligosaccharides as heparanase inhibitors
  作者：Zsuzsánna Csíki、Péter Fügedi

  DOI：10.1016/j.tet.2010.07.055

  日期：2010.9

  The synthesis of three azasugar-containing analogs of the disaccharide units of heparan sulfate, which are potential inhibitors of the enzyme heparanase, is reported. Synthetic routes were developed for the preparation of L-ido-nojirimycin type glycosyl acceptors with O-4 free. Glycosylation of these acceptors with an O-6 functionalized 2-azido-2-deoxy-n-glucose thioglycoside donor afforded the a-linked disaccharides in good yields. The advantages of using the 4-nitrobenzenesulfonyl group for the protection of the ring nitrogen of azasugars were demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.