(2R,3S,4R)-2-羟甲基四氢吡咯-3,4-二醇 | 100937-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2R,3S,4R)-2-羟甲基四氢吡咯-3,4-二醇
• 英文名称: (2R,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol
• 英文别名: (2R,3S,4R)-2hydroxymethyl-pyrrolidine-3,4-diol；1,4-dideoxy-1,4-imino-D-lyxitol
• CAS: 100937-51-7
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: OQEBIHBLFRADNM-WDCZJNDASA-N

物化性质

• 沸点：
  319.1±37.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 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

• 作为反应物：
  描述：

  (2R,3S,4R)-2-羟甲基四氢吡咯-3,4-二醇 在 盐酸 作用下， 以 水 为溶剂， 生成 (2R,3S,4R)-3,4-二羟基-2-(羟甲基)吡咯烷盐酸盐
  参考文献：
  名称：

  Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively

  摘要：

  Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-L-lyxitol (LIL). DIL showed potent [K-i = 0.13 mu M]-and LIL showed weak [K-i = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K-i = 64 mu M] and N-benzyl-LIL [K-i = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.004
• 作为产物：
  描述：

  (6R,7S,7aR)-6,7-二羟基四氢-1H-吡咯并[1,2-c][1,3]恶唑-3-酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以96%的产率得到(2R,3S,4R)-2-羟甲基四氢吡咯-3,4-二醇
  参考文献：
  名称：

  A New Strategy for the Diastereoselective Synthesis of Polyfunctionalized Pyrrolidines

  摘要：

  本文介绍了一种通过取代的 3-烯丙基-4-乙烯基-2-噁唑茚酮的闭环偏合成反应合成多官能度吡咯烷的新策略，以及随后对得到的吡咯并[1,2-c]噁唑-3-酮进行非对映选择性顺式二羟基化反应。

  DOI：

  10.1055/s-2003-43362

文献信息

• Stereoselective Aldol Additions Catalyzed by Dihydroxyacetone Phosphate-Dependent Aldolases in Emulsion Systems: Preparation and Structural Characterization of Linear and Cyclic Iminopolyols from Aminoaldehydes
  作者：Laia Espelt、Teodor Parella、Jordi Bujons、Conxita Solans、Jesús Joglar、Antonio Delgado、Pere Clapés

  DOI：10.1002/chem.200304966

  日期：2003.10.17

  hydroxyl group originating from the aldehyde. Characterization of the resulting iminocyclitols allowed the assessment of the diastereoselectivity of the enzymatic aldol reactions with respect to the N-protected aminoaldehyde. RAMA formed single diastereoisomers from N-Cbz-glycinal and from both enantiomers of N-Cbz-alaninal, while 14 % of the epimeric product was observed from N-Cbz-3-aminopropanal. Diastereoselectivity

  在许多情况下，磷酸二羟丙酮（DHAP）依赖性醛缩酶催化立体选择性醛缩醛加成的潜力受到受体醛在水/共溶剂混合物中的溶解度的限制。在这里，我们展示了乳液体系作为反应介质的效率，该反应介质是I类果糖-1,6-双磷酸醛缩醛醛糖酶（RAMA）和II类重组鼠李糖-1-磷酸醛糖醛缩醛醛糖酶从DHAP催化的DHAP之间的醛醇加成反应和N-苄氧基羰基（N-Cbz）氨基醛。相对于常规DMF /水混合物，乳液的使用将RAMA催化的羟醛转化率提高了三至十倍。无论反应介质如何，RhuA对N-Cbz氨基醛的反应性都比RAMA高。对于（S）-或（R）-Cbz-丙氨酸，RAMA表现出对R对映体的偏爱，而RhuA没有对映体歧视。将如此获得的线性N-Cbz氨基多元醇进行催化的分子内还原胺化，得到相应的亚氨基环醇。在所有检查的情况下，该反应都是非对映选择性的。面部选择性由源自醛的新形成的羟基的立体化学控制。所得亚氨基环醇的表征
• The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated Pyrrolidines
  作者：Yifang Huang、David R. Dalton、Patrick J. Carroll

  DOI：10.1021/jo962028s

  日期：1997.1.1

  (+)-serine or (-)-serine, as appropriate, convenient, high-yield, enantioselective synthesis of all eight stereoisomeric 2-hydroxymethyl-3,4-dihydroxypyrrolidines (the enantiomeric pairs of iminoribitol, -arabinitol, -xylitol, and -lyxitol) can be effected. The absolute configuration of the starting amino acid defines the set of azasugars produced.

  从（+）-丝氨酸或（-）-丝氨酸开始，视情况，方便，高产，对映选择性合成所有八个立体异构体2-羟甲基-3,4-二羟基吡咯烷酮（亚氨基核糖醇，-阿拉伯糖醇，-木糖醇的对映体对） ，和-lyxitol）。起始氨基酸的绝对构型定义了所产生的氮杂糖的集合。
• Synthesis of pyrrolidine iminosugars, (−)-lentiginosine, (−)-swainsonine and their 8a-epimers from d-glycals
  作者：Alafia A. Ansari、Y. D. Vankar

  DOI：10.1039/c3ra47555g

  日期：——

  Synthesis of pyrrolidine iminosugars has been described from D-glycals via dihydroxylation, oxidative cleavage and double nucleophilic displacement as the key steps. The pyrrolidines obtained have been utilized for the synthesis of important bicyclic iminosugars, viz. (−)-lentiginosine and (−)-swainsonine and their 8a-epimers, which are known to be glycosidase inhibitors.

  已经描述了由D-糖类通过二羟基化，氧化裂解和双亲核取代作为关键步骤从吡咯烷酮合成亚氨基糖。获得的吡咯烷已用于合成重要的双环亚氨基糖，即。（-）-lentiginosine和（-）-swainsonine及其8a-受体，已知是糖苷酶抑制剂。
• Aldol Additions of Dihydroxyacetone Phosphate to<i>N</i>-Cbz-Amino Aldehydes Catalyzed by<scp>L</scp>-Fuculose-1-Phosphate Aldolase in Emulsion Systems: Inversion of Stereoselectivity as a Function of the Acceptor Aldehyde
  作者：Laia Espelt、Jordi Bujons、Teodor Parella、Jordi Calveras、Jesús Joglar、Antonio Delgado、Pere Clapés

  DOI：10.1002/chem.200400648

  日期：2005.2.18

  FucA-catalyzed reactions. The N-protected aminopolyols thus obtained were converted to iminocyclitols by reductive amination with Pd/C. This reaction was highly diastereoselective with the exception of the reaction of the aldol adduct formed from (S)-N-Cbz-alaninal, which gave a 55:45 mixture of both epimers. From the stereochemical analysis of the resulting iminocyclitols, it was concluded that the

  研究了L-岩藻糖-1-磷酸醛缩酶（FucA）作为将磷酸二羟基丙酮酯（DHAP）不对称加成到N-保护的氨基醛中的催化剂的潜力。首先，在乳液体系和常规二甲基甲酰胺（DMF）/ H2O（1：4 v / v）混合物中研究了该反应。与DMF / （1：4）混合物中的反应相比，在100 mM DHAP下，乳液体系的使用导致FucA催化反应的转化率提高了2到3倍。通过用Pd / C还原胺化，将由此获得的N-保护的氨基多元醇转化为亚氨基环醇。该反应是高度非对映选择性的，除了由（S）-N-Cbz-丙氨酸形成的醛醇加合物的反应之外，这给出了两种差向异构体的55:45混合物。通过对所得亚氨基环醇的立体化学分析，结论是FucA催化的反应的立体选择性取决于N-Cbz-氨基醛受体的结构。与N-Cbz-丙氨酸的两个对映异构体的酶促醛醇缩合反应仅给出预期的3R，4R构型，而与N-Cbz-甘氨酸和N-Cbz的反应中产
• Redesign of the Phosphate Binding Site of L-Rhamnulose- 1-Phosphate Aldolase towards a Dihydroxyacetone Dependent Aldolase
  作者：Xavier Garrabou、Jesús Joglar、Teodor Parella、Ramon Crehuet、Jordi Bujons、Pere Clapés

  DOI：10.1002/adsc.201000719

  日期：2011.1.10

  The aldol addition of unphosphorylated dihydroxyacetone (DHA) to aldehydes catalyzed by L‐rhamnulose‐1‐phosphate aldolase (RhuA), a dihydroxyacetone phosphate‐dependent aldolase, is reported. Moreover, a single point mutation in the phosphate binding site of the RhuA wild type, that is, substitution of aspartate for asparagine at position N29, increased by 3‐fold the of aldol addition reactions of

  据报道，由L-鼠李糖-1-磷酸醛缩酶（RhuA）（一种依赖于磷酸二羟基丙酮的醛缩酶）催化的醛基中的未磷酸化二羟基丙酮（DHA）醛缩醛加成反应。此外，RhuA野生型磷酸结合位点的单点突变，即在N29位用天冬氨酸取代天冬酰胺，使DHA与其他醛受体而不是天然L的羟醛加成反应增加了3倍。丙醛 RhuA N29D突变体修改了天然底物的最佳酶设计，并改变了其催化性能，使醛缩酶比其他添加DHA的醛缩酶更具通用性。