2,3,4,5-tetra-O-acetyl-D-arabinoyl chloride | 3555-02-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,5-tetra-O-acetyl-D-arabinoyl chloride
• 英文别名: 2,3,4,5-tetra-O-acetyl-L-arabonyl chloride；tetra-O-acetyl-D-arabonic acid-chloride；Tetra-O-acetyl-D-arabonsaeure-chlorid；Tetraacetyl-D-arabonsaeurechlorid；[(2R,3R,4S)-2,3,4-triacetyloxy-5-chloro-5-oxopentyl] acetate
• CAS: 3555-02-0
• 化学式: C₁₃H₁₇ClO₉
• 分子量: 352.726
• InChiKey: RDULFPLUTJJIGL-UTUOFQBUSA-N

物化性质

• 熔点：
  74-75 °C
• 沸点：
  422.6±45.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-arabinoyl chloride 在 sodium azide 作用下， 以 丙酮 为溶剂， 生成 Tetra-O-acetyl-D-arabinonsaeureazid
  参考文献：
  名称：

  Bognar,R. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 680, p. 118 - 124

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-arabinoic acid 在 五氯化磷 作用下， 以 乙醚 为溶剂， 以70%的产率得到2,3,4,5-tetra-O-acetyl-D-arabinoyl chloride
  参考文献：
  名称：

  Synthesis of arabinitol 1-phosphate and its use for characterization of arabinitol–phosphate dehydrogenase

  摘要：

  D-Arabinitol 1-phosphate (Ara-oll-P), a substrate for D-arabinitol-phosphate dehydrogenase (APDH), was chemically synthesized from D-arabinonic acid in five steps (O-acetylation, chlorination, reduction, phosphorylation, and de-O-acetylation). Ara-oll-P was used as a substrate for the characterization of APDH from Bacillus halodurans. APDH converts Ara-oll-P to xylulose 5-phosphate in the oxidative reaction; both NAD(+) and NADP(+) were accepted as co-factors. Kinetic parameters for the oxidative and reductive reactions are consistent with a ternary complex mechanism. (c) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.030

文献信息

• Synthesis of some esters and lactones of aldonic acids
  作者：W.J. Humphlett

  DOI：10.1016/s0008-6215(00)82574-4

  日期：1967.4

  formation of esters of aldonic acids by treatment with an alcohol in the presence of an acid depends on the nature of the reagents and on the solubility of the products. The formation of aldonolactones is often a favored, competing reaction. Fully acetylated or benzoylated aldonic esters are formed without these restrictions. Among the products, liquid esters and certain of their acid chloride and

  摘要在酸存在下用醇处理可形成醛糖酸的酯，取决于试剂的性质和产物的溶解度。醛糖内酯的形成通常是有利的竞争反应。在没有这些限制的情况下，形成了完全乙酰化或苯甲酰化的醛糖酸酯。在产物中，液体酯及其某些酰氯和酰胺中间体是可蒸馏的。基于这项研究的结果，描述了一些合成酯和内酯的有效方法。
• Zhdanov,Yu.A. et al., Doklady Chemistry, 1971, vol. 197, p. 337 - 340
  作者：Zhdanov,Yu.A. et al.

  DOI：——

  日期：——
• Wolfrom; Brown; Evans, Journal of the American Chemical Society, 1943, vol. 65, p. 1022
  作者：Wolfrom、Brown、Evans

  DOI：——

  日期：——
• Tolstikov, G.A.; Krasteleva, I.V.; Spivak, A.Yu., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 7, p. 1313 - 1319
  作者：Tolstikov, G.A.、Krasteleva, I.V.、Spivak, A.Yu.、Shklyaev, Yu.V、Baikova, I.P.

  DOI：——

  日期：——
• Gakhokidze, R. A.; Fioliya, I. L., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 5, p. 953 - 956
  作者：Gakhokidze, R. A.、Fioliya, I. L.

  DOI：——

  日期：——