(2S,3R,4R,5R)-1-benzhydryl-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol | 132198-31-3

• 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,3R,4R,5R)-1-benzhydryl-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 132198-31-3
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: VWTMBCHKRFCFFM-UKBAYJJMSA-N

物化性质

• 沸点：
  551.2±50.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-1-benzhydryl-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol 在 palladium dihydroxide 氢气 作用下， 以91%的产率得到2,5-二(羟基甲基)-3,4-吡咯烷二醇
  参考文献：
  名称：

  一步法从二羰基糖中制得吡咯烷和哌啶氨基糖。1-deoxynojirimycin的简捷合成

  摘要：

  二羰基糖是通过双重还原胺化反应（NaCNBH 3，MeOH）进行立体选择性合成羟基化哌啶和吡咯烷的便​​利底物。使用这种策略，由5-酮-D-果糖（2，可商购）和5-酮-D-葡萄糖（2，5-脱水亚氨基-D-葡萄糖醇（1）和1-脱氧野rim霉素（3））制备。4）。

  DOI：

  10.1016/s0040-4039(00)97169-7
• 作为产物：
  描述：

  fructopyranose 在 sodium tetrahydroborate 、 culture of Gluconobactor cerinus (ATCC catalogue number IFO 3267) 作用下， 生成 (2S,3R,4R,5R)-1-benzhydryl-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  Antibody-catalysed glycosyl transfer reactions from in vitro immunization

  摘要：

  使用五元环亚胺环醇在体外进行免疫，获得了能够催化对硝基苯基吡喃葡萄糖苷和对硝基苯基吡喃半乳糖苷水解的抗体，其速率增益（kcat/kuncat）超过10,000倍。

  DOI：

  10.1039/a704885h

文献信息

• The Total Synthesis of Allosamidin. Expansions of the Methodology of Azaglycosylation Pursuant to the Total Synthesis of Allosamidin. A Surprising Enantiotopic Sense for a Lipase-Induced Deacetylation
  作者：David A. Griffith、Samuel J. Danishefsky

  DOI：10.1021/ja960526c

  日期：1996.1.1

  Allosamidin, recently isolated from mycelial extracts of Streptomyces sp. 1713, is a powerful and selective chitinase inhibitor. The total synthesis of allosamidin is described herein. The electric eel acetylcholinesterase-mediated enantioselective hydrolysis of (trans,trans)-2-(benzyloxy)cyclopentene-1,3-diol diacetate accessed a monoacetyl derivative. Five additional steps produced a protected version

  Allosamidin，最近从 Streptomyces sp. 的菌丝体提取物中分离出来。1713，是一种强效选择性几丁质酶抑制剂。Allosamidin 的全合成在此描述。电鳗乙酰胆碱酯酶介导的 (trans,trans)-2-(benzyloxy)cyclopentene-1,3-diol diacetate 的对映选择性水解获得了单乙酰衍生物。五个额外的步骤产生了受保护版本的异沙脒苷元（“allosamizoline”）部分。Allal 衍生物与苯磺酰胺在卤源存在下立体选择性地反应，得到 2β-halo-1α-sulfonamidohexose。用强碱处理该产物生成中间体 1,2-磺酰氮丙啶，其被保护的丙二醛衍生物捕获以提供二糖甘氨酸。重申该方案可以获得所需的三糖。脱保护后，完成了异沙脒的全合成。此外，该方法经过修改后，可以获得几种异氨基丁酸...
• Pyrrolidine and piperidine aminosugars from dicarbonyl sugars in one step. Concise synthesis of 1-deoxynojirimycin
  作者：Allen B. Reitz、Ellen W. Baxter

  DOI：10.1016/s0040-4039(00)97169-7

  日期：1990.1

  Dicarbonyl sugars are convenient substrates for the stereoselective synthesis of hydroxylated piperidines and pyrrolidines, via a double reductive amination reaction (NaCNBH3, MeOH). Using this strategy, 2,5-anhydro-imino-D-glucitol (1) and 1-deoxynojirimycin (3) were prepared from 5-keto-D-fructose (2, commercially available) and 5-keto-D-glucose (4), respectively.

  二羰基糖是通过双重还原胺化反应（NaCNBH 3，MeOH）进行立体选择性合成羟基化哌啶和吡咯烷的便​​利底物。使用这种策略，由5-酮-D-果糖（2，可商购）和5-酮-D-葡萄糖（2，5-脱水亚氨基-D-葡萄糖醇（1）和1-脱氧野rim霉素（3））制备。4）。
• A search for pyrophosphate mimics for the development of substrates and inhibitors of glycosyltransferases
  作者：Ruo Wang、Darryl H. Steensma、Yoshikazu Takaoka、Joanne W. Yun、Tetsuya Kajimoto、Chi-Huey Wong

  DOI：10.1016/s0968-0896(97)00005-9

  日期：1997.4

  The design and synthesis of several beta-1,4-galactosyltransferase inhibitors are reported. Mimics of the pyrophosphate-Mn2+ complex were the focus of the design. Malonic, tartaric, and monosaccharide moieties were used as replacements of the pyrophosphate moiety, and galactose or azasugars with potent galactosidase inhibitory activity were used as the 'donor' component. Compound 6, in which glucose

  报道了几种β-1，4-半乳糖基转移酶抑制剂的设计和合成。焦磷酸盐-Mn2 +配合物的模拟物是设计的重点。丙二酸，酒石酸和单糖部分被用作焦磷酸盐部分的替代物，而具有有效的半乳糖苷酶抑制活性的半乳糖或氮杂糖被用作“供体”组分。以葡萄糖为焦磷酸盐-Mn2 +复合物模拟物，以半乳糖为“供体”成分的化合物6对转移酶表现出最佳的抑制活性，Ki为119.6 microM。
• Expeditious Synthesis of Aza sugars by the Double Reductive Amination of Dicarbonyl Sugars
  作者：Ellen W. Baxter、Allen B. Reitz

  DOI：10.1021/jo00090a040

  日期：1994.6

  Polyhydroxylated pyrrolidines and piperidines were prepared by the double reductive amination of dicarbonyl, sugars with primary amines and NaCNBH3 in MeOH. Stereocontrol in these reactions depended on the nature of the amine and dicarbonyl sugar. For example, 5-keto-D-fructose (7) gave three pyrrolidine stereoisomers, with the N-alkylated 2,5-anhydro-2,5-imino-D-glucitol predominating. Under similar reaction conditions with benzhydrylamine, 5-keto-D-glucose (20) afforded a 96:4 mixture of piperidines favoring D-gluco 25A, whereas 5-keto-D-mannose (6) produced a 67:33 mixture enriched in D-manno isomer 40. This method allowed for the direct and relatively short synthesis of 1-deoxynojirimycin (DNJ, 1) and 1-deoxymannojirimycin (DMJ, 5) and N-alkylated derivatives thereof. Similar reactions with O-protected 5-keto-D-glucose derivatives 21 and 22 were less stereoselective and lower yielding.
• Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors
  作者：Chi-Huey Wong、Louis Provencher、John A. Porco、Sang-Hun Jung、Yi-Fong Wang、Lihren Chen、Ruo Wang、Darryl H. Steensma

  DOI：10.1021/jo00111a007

  日期：1995.3

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.