L-erythrose | 210230-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-erythrose
• 英文别名: (3S,4S)-oxolane-2,3,4-triol
• CAS: 210230-62-9
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: FMAORJIQYMIRHF-LPGMDIISSA-N

物化性质

• 沸点：
  290.6±40.0 °C(Predicted)
• 密度：
  1.698±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-erythrose 在 glucose isomerase (EC 5.3.1.5) 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 8.0h， 以39%的产率得到L(+)-赤藓酮糖(水合)
  参考文献：
  名称：

  Glucose isomerase catalysed isomerisation reactions of (2R,3R)-configured aldofuranoses into the corresponding open-chain 2-ketoses

  摘要：

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R)-configured aldofuranoses such as D-erythrose, as well as homologous C-5-modified D-ribose derivatives, as substrates. In the case of D-erythrose, quantitative conversion into D-glycero-tetrulose took place. D-Ribofuranoses were converted into the corresponding open-chain 2-ketoses in isolated yields of 65%. Surprisingly, L-erythrose also turned out to be a substrate of this enzyme. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00206-1
• 作为产物：
  描述：

  2,3-O-isopropylidene-L-erythrofuranose 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 6.0h， 生成 L-erythrose
  参考文献：
  名称：

  对映体全合成（-）-crotanecine

  摘要：

  Crotanecine是许多吡咯烷核生物碱的烟碱基础成分。该烟酸亚基是带有伯烯丙基醇的氨基三醇，其特征在于其立体中心的全顺式关系。使用核糖作为手性起点的简单而通用的环构建方法已经完成了克罗他辛的合成。

  DOI：

  10.1016/j.tetlet.2017.08.056

文献信息

• Indium- and Zinc-Mediated Acyloxyallylation of Protected and Unprotected Aldotetroses—Revealing a Pronounced Diastereodivergence and a Fundamental Difference in the Performance of the Mediating Metal
  作者：Markus Draskovits、Christian Stanetty、Ian R. Baxendale、Marko D. Mihovilovic

  DOI：10.1021/acs.joc.7b03063

  日期：2018.3.2

  were successfully applied to the indium and also zinc-mediated acyloxyallylation, with the latter being a first for an unprotected sugar. The investigation largely benefited from the choice of these more exotic starting materials as it allowed unambiguous identification/quantification of the hexose-products which are available as authentic reference materials. The observed diastereoselectivities indicate

  十多年前，未经保护的醛糖的酰氧基化首次被证实为还原糖的潜在的优雅的二碳同系物（通过臭氧分解）。但是，它在实际案例合成中的应用仍然很少。在如此成功的展示之后，我们回答了有关这一有吸引力的转变的几个悬而未决的问题，我们进行了深入的方法学重新调查。将未受保护和受保护形式的差向异构体四聚体l-赤藓糖和d-苏糖成功应用于铟以及锌介导的酰氧基烯丙基化，后者是未保护糖的首创。该研究很大程度上得益于这些更具异国情调的起始原料的选择，因为它可以对己糖产品进行明确的鉴定/定量，而后者可作为可靠的参考材料。观察到的非对映选择性表明对底物有很强的控制作用（O2处的立体化学），并详细研究了试剂结构对选择性的影响。相关保护和未保护结构之间存在强烈的面部非对映差异，并且铟和锌之间的性能表现出乎意料的显着差异。
• Total Synthesis of Asperchalasines A, D, E, and H
  作者：Xianwen Long、Yiming Ding、Jun Deng

  DOI：10.1002/anie.201808481

  日期：2018.10.22

  The first total syntheses of the cytochalasan dimers asperchalasines A, D, E, and H have been accomplished. The key steps of the synthesis include a highly stereoselective intermolecular Diels–Alder reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B, and an intermolecular Diels–Alder reaction followed by a biomimetic oxidative heterodimerization by 5+2

  已经完成了细胞chalasan二聚体的第一个总合成，即asperchalasines A，D，E和H。合成的关键步骤包括高度立体选择性的分子间Diels-Alder反应和Horner-Wadsworth-Emmons大环化以建立关键单体天冬氨酸蛋白酶B，分子间的Diels-Alder反应，然后通过5 + 2环加成仿生氧化异二聚提供Asperchalasine A.的合成努力为细胞松弛素二聚体的生物合成途径提供了见识，并使其生物学特性得以进一步研究。
• Syntheses of ethyl 3-deoxy-3,3-difluoro-d-arabino-heptulosonate and analogues
  作者：Yuan Li、Michael G.B Drew、Elizabeth V Welchman、Rajeev K Shirvastava、Shende Jiang、Roy Valentine、Gurdial Singh

  DOI：10.1016/j.tet.2004.06.048

  日期：2004.7

  The difluormated analogues of 3-deoxy-D-arabino-heptulosonic acid (DAH) 12, 24 and its enantiomer have been synthesised from D- and L-crythrose via a Reformatsky reaction which gave a mixture of diastereoiosmers in favour of the anti isomer. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and Antiviral Evaluation of Halogenated β-<scp>d</scp>- and -<scp>l</scp>-Erythrofuranosylbenzimidazoles
  作者：Kristjan S. Gudmundsson、Jeffrey Tidwell、Nicole Lippa、George W. Koszalka、Nanine van Draanen、Roger G. Ptak、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jm990195p

  日期：2000.6.1

  A series of 2-substituted benzimidazole D- and L-erythrofuranosyl nucleosides were synthesized and tested for activity against herpesviruses and for cytotoxicity. The D-nucleosides 2,5,6-trichloro-1-(beta-D-erythrofuranosyl)benzimidazole (8a) and 2-bromo-5,6-dichloro-1-(beta-D-erythrofuranosyl)benzimidazole (8b) were prepared by coupling 1,2,3,-tri-O-acetyl-beta-D-erythrofuranose (D-6) with the appropriate benzimidazole, followed by removal of the acetyl protecting groups. The 2-isopropylamino (9), 2-cyclopropylamino (10), and 2-mercaptobenzyl (11) derivatives were synthesized by nucleophilic displacements of the C-2 chlorine in the benzimidazole moiety of 8a. The D-nucleoside 4-bromo-5,6-dichloro-2-isopropylamino-1-(beta-D-erythrofuranosyl)benzimidazole (17) was prepared by coupling D-6 with the appropriate benzimidazole. The L-erythrofuranosyl derivatives, 5,6-dichloro-2-isopropylamino-1-(beta-L-erythrofuranosyl)benzimidazole (21a), its 2-cyclopropylamine analogue (21b), and the 2-isopropylamino analogue (4c). In comparison, 8a was 15-fold more active against HCMV than 4a, and 8b was 4-fold more active against HCMV than 4b. The 5,6-dichloro-2-isopropylamino-1-(beta-L-erythrofuranosyl)benzimidazole (21a) was less active than 4c, which is now in clinical trials for HCMV infection. Both 8a,b had comparable HCMV activity to 4c. Mode of action studies with the D-erythrose analogues established that 8b acted by inhibition of viral DNA processing whereas 9 and 10 may act via a different mechanism. The lack of a 5'-hydroxymethyl group in all members of this series established that antiviral activity occurred without 5'-phosphorylation, a feature required for the activity of most nucleoside analogues.
• A convenient synthesis of l-erythrose
  作者：Ramesh H. Shah

  DOI：10.1016/s0008-6215(00)90148-4

  日期：1986.11