3-O-benzyl-2-deoxy-D-ribonolactone | 91879-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-benzyl-2-deoxy-D-ribonolactone
• 英文别名: (4S,5R)-5-(hydroxymethyl)-4-phenylmethoxyoxolan-2-one
• CAS: 91879-31-1
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: WHMXBMHPTAAQHO-WDEREUQCSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  415.6±35.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-2-deoxy-D-ribonolactone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以96%的产率得到D-(+)-核糖酸-gamma-内酯
  参考文献：
  名称：

  Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl- 4-butanolides in Relation to PGE₂

  摘要：

  Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [H-3]-PGE(2) binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2). Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.

  DOI：

  10.1021/jm034216y
• 作为产物：
  描述：

  (E)-5-((tert-butyldiphenylsilyl)oxy)pent-2-en-1-ol 在 4 A molecular sieve chromium(VI) oxide 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(-)-diethyl tartrate 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 72.5h， 生成 3-O-benzyl-2-deoxy-D-ribonolactone
  参考文献：
  名称：

  Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl- 4-butanolides in Relation to PGE₂

  摘要：

  Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [H-3]-PGE(2) binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2). Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.

  DOI：

  10.1021/jm034216y

文献信息

• Teng, Kelly; Marquez, Victor E.; Milne, George W. A., Journal of the American Chemical Society, 1992, vol. 114, # 3, p. 1059 - 1070
  作者：Teng, Kelly、Marquez, Victor E.、Milne, George W. A.、Barchi Jr., Joseph J.、Kazanietz, Marcelo G.、Lewin, Nancy E.、Blumberg, Peter M.、Abushanab, Elie

  DOI：——

  日期：——
• Mulzer, Johann; Kappert, Michael; Huttner, Gottfried, Angewandte Chemie, 1984, vol. 96, # 9, p. 726 - 727
  作者：Mulzer, Johann、Kappert, Michael、Huttner, Gottfried、Jibril, Ibrahim

  DOI：——

  日期：——
• MULZER, J.;KOPPERT, M.;HUTTNER, G.;JIBRIL, I., ANGEW. CHEM., 1984, 96, N 9, 726-727
  作者：MULZER, J.、KOPPERT, M.、HUTTNER, G.、JIBRIL, I.

  DOI：——

  日期：——
• Enantioselective Synthesis and Biological Activity of (3<i>S</i>,4<i>R</i>)- and (3<i>S</i>,4<i>S</i>)-3-Hydroxy-4-hydroxymethyl- 4-butanolides in Relation to PGE₂
  作者：Pedro O. Miranda、Francisco Estévez、José Quintana、Candelaria I. García、Ignacio Brouard、Juan I. Padrón、Juan P. Pivel、Jaime Bermejo

  DOI：10.1021/jm034216y

  日期：2004.1.1

  Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [H-3]-PGE(2) binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2). Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.