2(R)-methyl,5(S)-(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine | 135395-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2(R)-methyl,5(S)-(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
• 英文别名: (2S,3R,4R,5R)-3,4-dihydroxy-2-(hydroxymethyl)-5-methylpyrrolidine；2,5,6-trideoxy-2,5-imino-D-glucitol；(2S,3R,4R,5R)-2-(hydroxymethyl)-5-methylpyrrolidine-3,4-diol；(2r,3r,4r,5s)-2-Methyl-5-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 135395-54-9
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: YRBKDBZXOAEMOT-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3R,4R)-2,3,5-tri-O-benzyl-4-O-formyl-pentanal 在 盐酸 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium cyanoborohydride 、 zinc(II) chloride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 2(R)-methyl,5(S)-(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
  参考文献：
  名称：

  由D-糖类合成二羟基和三羟基脯氨酸衍生物：在合成多取代的吡咯烷并生物活性的1C-芳基/烷基吡咯烷中的应用

  摘要：

  从D-糖和2C-甲酰基-糖合成了六种不同类型的O-苄基保护的脯氨酸衍生物。一种二-O-苄基保护的脯氨酸衍生物已被用于通过立体选择性方式通过[3 + 2]环加成反应合成多取代的吡咯并核苷。此外，我们还报告了通过多种D的双重还原胺化反应，对具有生物活性的1C-芳基/烷基吡咯烷（即4-上消旋胺B，4-上消旋胺A，1C丁基和1C-甲基吡咯烷）进行立体选择性合成的报道。 -葡萄糖衍生的二酮与对甲氧基苄胺。

  DOI：

  10.1016/j.carres.2019.02.004

文献信息

• Diversity-Oriented Synthesis of Useful Chiral Building Blocks from D-Mannitol
  作者：Appu Aravind、Ponminor Senthil Kumar、Muthukumar Gomathi Sankar、Sundarababu Baskaran

  DOI：10.1002/ejoc.201100968

  日期：2011.12

  A diversity-oriented synthesis is described for functionalized chiral building blocks (i.e., 7, 9, 10, 16, and 17) and the biologically active iminosugar, fucosidase inhibitor (2S,3R,4R,5R)-2-(hydroxymethyl)-5-methylpyrrolidine-3,4-diol (22), starting from common chiral intermediate 1a which is obtained through a regioselective reductive cleavage of a bis(benzylidene) acetal.

  描述了功能化手性构件（即 7、9、10、16 和 17）和生物活性亚氨基糖、岩藻糖苷酶抑制剂 (2S,3R,4R,5R)-2-(羟甲基)-的面向多样性的合成5-甲基吡咯烷-3,4-二醇 (22)，从常见的手性中间体 1a 开始，该中间体是通过双（亚苄基）缩醛的区域选择性还原裂解获得的。
• Polyhydroxylated Pyrrolidines: Synthesis of Trideoxy-2,5-iminohexitols
  作者：Isidoro Izquierdo、María Plaza、Juan Tamayo、Daniele Lo Re、Fernando Sánchez-Cantalejo

  DOI：10.1055/s-2008-1072566

  日期：2008.5

  A series of naturally occurring pyrrolidine alkaloids and analogues, with the general structure of trideoxy-2,5-iminohexitols (imino- or azasugars), have been enantiosynthesized using triorthogonally protected pyrrolidines, previously prepared from commercial d-fructose, as homochiral starting materials. The inhibitory activity of some of the described compounds against glycosidases and glycosyltransferases makes them potential therapeutic agents.

  利用以前从商用 d-果糖中制备的三正对映体保护的吡咯烷作为同手性起始原料，合成了一系列天然存在的吡咯烷生物碱和类似物，其一般结构为三脱氧-2,5-亚氨基己糖醇（亚氨基或氮杂杉糖）。其中一些化合物对糖苷酶和糖基转移酶具有抑制活性，因此具有潜在的治疗作用。
• Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars
  作者：Kevin K. C. Liu、Tetsuya Kajimoto、Lihren Chen、Ziyang Zhong、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/jo00022a013

  日期：1991.10

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.
• Kajimoto, Tetsuya; Chen, Lihren; Liu, Kevin K.-C., Journal of the American Chemical Society, 1991, vol. 113, # 18, p. 6678 - 6680
  作者：Kajimoto, Tetsuya、Chen, Lihren、Liu, Kevin K.-C.、Wong, Chi-Huey

  DOI：——

  日期：——
• Synthesis of di- and trihydroxy proline derivatives from D-glycals: Application in the synthesis of polysubstituted pyrrolizidines and bioactive 1C-aryl/alkyl pyrrolidines
  作者：Ashish Kumar Verma、Sateesh Dubbu、Ande Chennaiah、Yashwant D. Vankar

  DOI：10.1016/j.carres.2019.02.004

  日期：2019.3

  O-benzyl protected proline derivatives have been synthesized from D-glycals and 2C-formyl-glycals. One of the di-O-benzyl protected proline derivatives has been utilized for the synthesis of polysubstituted pyrrolizidines via [3 + 2] cycloaddition in a stereoselective manner. Further, we also report on the stereoselective synthesis of biologically active 1C-aryl/alkyl pyrrolidines i.e. 4-epi-radicamine

  从D-糖和2C-甲酰基-糖合成了六种不同类型的O-苄基保护的脯氨酸衍生物。一种二-O-苄基保护的脯氨酸衍生物已被用于通过立体选择性方式通过[3 + 2]环加成反应合成多取代的吡咯并核苷。此外，我们还报告了通过多种D的双重还原胺化反应，对具有生物活性的1C-芳基/烷基吡咯烷（即4-上消旋胺B，4-上消旋胺A，1C丁基和1C-甲基吡咯烷）进行立体选择性合成的报道。 -葡萄糖衍生的二酮与对甲氧基苄胺。