2-deoxy-D-erythro-pentafuranose | 130778-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-deoxy-D-erythro-pentafuranose
• 英文别名: (4S)-Tetrahydrofuran-2,4-diol；(4S)-oxolane-2,4-diol
• CAS: 130778-53-9；134864-45-2；141206-90-8
• 化学式: C₄H₈O₃
• 分子量: 104.106
• InChiKey: JLQZBFCQUPAOJC-WUCPZUCCSA-N

物化性质

• 沸点：
  275.7±40.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  7
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-丙二硫醇 、 2-deoxy-D-erythro-pentafuranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以77%的产率得到(S)-2-(2',3'-dihydroxypropyl)-1,3-dithiane
  参考文献：
  名称：

  Total synthesis of maytansinoids. Approach to 4,6-bisdemethylmaytansine and 4-demethylmaytansine

  摘要：

  A convergent strategy was elaborated to synthesize maytansine 1 and maytansinoids modified on the carbon skeleton, especially 4-demethylmaytansine 2, 6-demethylmaytansine 3, 4,6-bisdemethylmaytansine 4. In this paper, the feasibility of the project was verified by the preparation of key intermediates for the synthesis of 4, 6-bisdemethylmaytansine and 6-demethylmaytansine. The C-1-N open chain compound 18 in the 4,6-bisdemethyl series was obtained.

  DOI：

  10.1016/s0040-4020(01)88513-6
• 作为产物：
  描述：

  (4S)-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-ol 在 四丁基氟化铵 作用下， 生成 2-deoxy-D-erythro-pentafuranose
  参考文献：
  名称：

  Development of Noviomimetics as C-Terminal Hsp90 Inhibitors

  摘要：

  KU-32 and KU-596 are novobiocin-derived, C terminal heat shock protein 90 (Hsp90) modulators that induce Hsp70 levels and manifest neuroprotective activity. However, the synthetically complex noviose sugar requires 10 steps to prepare, which makes translational development difficult. In this study, we developed a series of "noviomimetic" analogues of KU-596, which contain noviose surrogates that can be easily prepared, while maintaining the ability to induce Hsp70 levels. Both sugar and sugar analogues were designed, synthesized, and evaluated in a luciferase reporter assay, which identified compound 37, a benzyl containing noviomimetic, as the most potent inducer of Hsp70.

  DOI：

  10.1021/acsmedchemlett.5b00331

文献信息

• Unprecedented Asymmetric Aldol Reactions with Three Aldehyde Substrates Catalyzed by 2-Deoxyribose-5-phosphate Aldolase
  作者：Harrie J. M. Gijsen、Chi-Huey Wong

  DOI：10.1021/ja00097a082

  日期：1994.9
• Sequential Three- and Four-Substrate Aldol Reactions Catalyzed by Aldolases
  作者：Harrie J. M. Gijsen、Chi-Huey Wong

  DOI：10.1021/ja00134a001

  日期：1995.7

  This paper describes a useful synthetic strategy based on sequential enzyme-catalyzed aldol addition reactions. The aldol reaction of an acceptor aldehyde with acetaldehyde, catalyzed by 2-deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4), gives a new aldehyde, which subsequently reacts with a second donor substrate, catalyzed by DERA or another aldolase. This sequential aldol reaction proceeds because of the formation of a stable cyclic hemiacetal or hemiketal product. In this way several 6-substituted 2,4,6-trideoxyhexoses have been stereoselectively synthesized via a one-pot double DERA-catalyzed reaction. DERA coupled with fructose-1,6-diphosphate aldolase from rabbit muscle (RAMA, EC 4.1.2.13) in a one-pot reaction gave a variety of 5-deoxyheptuloses, however not in 100% stereoselectivity. The sequential aldol reactions with four substrates were accomplished by coupling DERA with N-acetylneuraminic acid aldolase (NeuAc aldolase, EC 4.1.3.3) to give several nine-carbon sialic acid-type sugar derivatives.