2-Acetoxy-propionic acid (2S,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 141171-34-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2-Acetoxy-propionic acid (2S,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl 2-acetyloxypropanoate
• CAS: 141171-34-8
• 化学式: C₁₆H₂₁N₃O₇
• 分子量: 367.359
• InChiKey: HORCFTMZKWKFQE-RAYMKUHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-(-)-2-acetoxypropanoyl bromide 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 2-Acetoxy-propionic acid (2S,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Syntheses of the anti-AIDS drug 2',3'-dideoxycytidine from cytidine

  摘要：

  Two efficient syntheses of the anti-AIDS drug 2',3'-dideoxycytidine (3) from N4-acetylcytidine (4) are described. In one, silylation of the C-5' hydroxyl group of 4 with tert-butyldimethylsilyl chloride followed by treatment with 1',1'-(thiocarbonyl)diimidazole gave the cyclic thionocarbonate 7, which on reaction with 1,3-dimethyl-2-phenyl-1,3-diazaphospholidine gave the crystalline alkene 8. Hydrogenation of 8, followed by desilylation with tetrabutylammonium fluoride and hydrolysis, gave 3 in 27% overall yield from 4. In the other synthesis, 4 was converted into a regioisomeric mixture of bromo acetates 11 with 2-acetoxy-2-methylpropanoyl bromide. Reductive elimination of 11 with zinc-copper couple in acetic acid or electrochemically gave the crystalline alkene 15, whose stereostructure was established by a single-crystal X-ray analysis. Hydrogenation of 15, followed by hydrolysis, gave ddC (3). In a through process, which is suitable for large-scale work, this second synthesis gave 3 in over 40% overall yield from 4. The use of (S)-(-)-2-acetoxypropanoyl bromide, of 2-acetoxybenzoyl bromide, and of hydrogen bromide/acetic acid in the bromoacetylation of 4 is also described.

  DOI：

  10.1021/jo00038a042

文献信息

• BELICA, PETER S.;HUANG, TAI-NANG;MANCHAND, PERSY S.;PARTRIDGE, JOHN J.;TA+
  作者：BELICA, PETER S.、HUANG, TAI-NANG、MANCHAND, PERSY S.、PARTRIDGE, JOHN J.、TA+

  DOI：——

  日期：——