(2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin | 100806-55-1

• 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: (2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin
• 英文别名: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-L-arabitinol；2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-L-arabinitol；(2S,3S,4S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)pyrrolidine
• CAS: 100806-55-1
• 化学式: C₂₆H₂₉NO₃
• 分子量: 403.521
• InChiKey: GNMPTPJZKQHGBR-GSDHBNRESA-N

物化性质

• 沸点：
  526.7±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin 在 钯 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 1,4-二脱氧-1,4-亚氨基阿拉伯糖醇
  参考文献：
  名称：

  Potent competitive inhibition of α-galactosidase and α-glucosidase activity by 1,4-dideoxy-1,4-iminopentitols: syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol and of both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol

  摘要：

  DOI：

  10.1016/s0040-4039(00)98636-2
• 作为产物：
  描述：

  (2R,3R)-diethyl 2,3-bis(benzyloxy)succinate 在 三乙基硅烷 、 lithium hydroxide 、 lithium aluminium tetrahydride 、 samarium diiodide 、 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 三氯化铁 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 20.5h， 生成 (2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin
  参考文献：
  名称：

  A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

  摘要：

  A highly diastereoselective synthesis of enantio-enriched all trans-3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O,O'-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB 1 (1), LAB 1 (2), N-hydroxyethyl-DAB 1 (4), 6-deoxy-DMDP 7, and 5-epi-radicamine B 36 as well as the reductive ring-opening product 35. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.02.087

文献信息

• Novel alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0389723A1

  公开（公告）日：1990-10-03

  This invention relates to novel N-derivatives, of 1,4-di-­deoxy-1,4-imino-L-arabinitol (I), to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes. wherein n is zero, one or two, and R is a glycosyl or etherified or acylated glycosyl radical containing from 1 to 3 hexose or pentose units, said glycosyl radical optionally bearing an ether or ester derivative of the hydroxyl moiety located on the anomeric carbon atom.

  本发明涉及新颖的1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇（I）的N-衍生物，涉及其制备方法及其最终用途，特别是作为治疗糖尿病的用途。 其中n为0、1或2，R为含有1至3个己糖或戊糖单元的糖基或醚化或酰化的糖基基团，所述糖基基团任选地在其异头碳原子上的羟基部分带有醚或酯衍生物。
• GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME
  申请人：Pinto M. Brian

  公开号：US20070244184A1

  公开（公告）日：2007-10-18

  The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

  本发明的化合物涉及与salacinol的链延伸和链修饰类似物，包括其中硫酸酯基团已被羧酸酯基团或磷酸酯基团取代的实施例。在其他实施例中，硫酸酯基团在带电离结构中已被向一碳原子移位。在另一实施例中，多羟基侧链可以被脂溶性烷基链和适当的对离子取代。本发明还涵盖了合成salacinol类似物的方法以及将这些类似物用于酶抑制应用的方法。
• Synthesis, enzymatic activity, and X-ray crystallography of an unusual class of amino acids
  作者：Wang Chen、Douglas A. Kuntz、Tamika Hamlet、Lyann Sim、David R. Rose、B. Mario Pinto

  DOI：10.1016/j.bmc.2006.09.004

  日期：2006.12

  synthesis of two novel amino acids, nitrogen analogues of the naturally occurring glycosidase inhibitor, salacinol, containing a carboxylate inner salt are described, along with the crystal structure of one of these analogues in the active site of Drosophila melanogaster Golgi mannosidase II (dGMII). Salacinol, a naturally occurring sulfonium ion, is one of the active principals in the aqueous extracts of Salacia

  描述了两种新氨基酸，天然糖苷酶抑制剂的氮类似物salacinol的合成，其中含有羧酸盐内盐，以及果蝇果蝇高尔基甘露糖苷酶II（dGMII）活性位点中这些类似物之一的晶体结构。 。Salacinol是天然存在的sulf离子，是Salacia reticulata水提取物中的活性成分之一，传统上在斯里兰卡和印度用于治疗糖尿病。合成策略依赖于2,5,5-脱水- 2,3-二-O-苄基-1-抗坏血酸产生偶联的加合物。脱保护，立体选择性催化还原和偶联产物的水解得到目标化合物。衍生自d-阿拉伯糖醇的化合物抑制dGMII（糖蛋白加工途径中的关键酶之一），IC（50）为0.3mM。抑制GMII已被确定为控制转移性癌症的靶标。该化合物与dGMII的复合物的X射线晶体结构提供了对有效抑制剂的需求的见解。相同的化合物抑制重组人麦芽糖酶葡糖淀粉酶，后者是参与小肠中葡萄糖寡糖分解的关键肠酶之一，K（i）值为21mic
• Concise Synthesis of 1,4-Dideoxy-1,4-imino-l-arabinitol (LAB) from d-Xylose by Intramolecular Stereospecific Substitution of a Hydroxy Group
  作者：Sunisa Akkarasamiyo、Hatairat Promsaka Na Sakonnakhon、Punlop Kuntiyong、Poonsakdi Ploypradith、Joseph S. M. Samec

  DOI：10.1055/s-0041-1738432

  日期：2023.3

  We report a concise and green total synthesis of 1,4-dideoxy-1,4-imino-l-arabinitol hydrochloride from naturally occurring d-xylose. The key step involves a stereospecific substitution of a hydroxy group, without prior derivatization, in which the only byproduct is water. This opens up a novel benign route to iminosugar derivatives with diverse biological activities.

  我们报告了 1,4-dideoxy-1,4-imino- 的简洁绿色全合成升- 天然存在的盐酸阿拉伯糖醇d-木糖。关键步骤涉及羟基的立体特异性取代，无需事先衍生化，其中唯一的副产物是水。这为具有多种生物活性的亚氨基糖衍生物开辟了一条新的良性途径。
• Investigation of the enantioselectivity of acetylcholinesterase and butyrylcholinesterase upon inhibition by tacrine-iminosugar heterodimers
  作者：I. Caroline Vaaland、Óscar López、Adrián Puerta、Miguel X. Fernandes、José M. Padrón、José G. Fernández-Bolaños、Magne O. Sydnes、Emil Lindbäck

  DOI：10.1080/14756366.2022.2150762

  日期：2023.12.31