3-(D-Ribosyl)-4-hydroxyhexahydropyrimidine-2-thione | 99677-77-7

• 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: 3-(D-Ribosyl)-4-hydroxyhexahydropyrimidine-2-thione
• 英文别名: 1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-1,3-diazinane-2-thione
• CAS: 99677-77-7
• 化学式: C₉H₁₆N₂O₅S
• 分子量: 264.302
• InChiKey: ABHLDPBNSGKFHE-DJAUARBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(D-Ribosyl)-4-hydroxyhexahydropyrimidine-2-thione 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.4h， 以51.1%的产率得到(6S)-6,2'-anhydro-6-hydroxy-1-(α-D-ribofuranosyl)hexahydropyrimidine-2-thione
  参考文献：
  名称：

  New Pyrimidine Cyclonucleosides with Hydrogenated Aglycones: Synthesis and X-Ray Structures

  摘要：

  Acid catalysed transformations of (6S)-6,5'-anhydro-6-hydroxy-1-(2',3'-O-isopropylidene-beta -D-ribofuranosyl)hexahydropyrimidine-2-thione are studied. (6R)-6,2'-anhydro-6-hydroxy-1-(alpha -D-ribofuranosyl)hexahydropyrimidine-2-thione was formed as a thermodynamically stable product. Two intermediates, (6S)-6,5'-anhydro-6-hydroxy-1-(beta -D-ribofuranosyl)hexahydropyrimidine-2-thione and 6-hydroxy-1-(D-ribosyl)hexahydropyrimidine-2-thione and products of cleavage of glycosidic bond were identified in the reaction mixtures. Results of X-ray structural determination of the synthesised nucleosides are presented.

  DOI：

  10.1080/15257770008045464
• 作为产物：
  描述：

  2,3,5-Tri-O-acetyl-β-D-ribofuranosyl isothiocyanate 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 9.0h， 生成 3-(D-Ribosyl)-4-hydroxyhexahydropyrimidine-2-thione
  参考文献：
  名称：

  N-glycosides. V. 3-glycosyl-4-hydroxyhexahydropyrimidine-2-thiones and their acyclic glycosylthiourea precursors as stimulators of non-specific resistance to infection

  摘要：

  DOI：

  10.1007/bf01148382

文献信息

• Synthesis of 4,5-'anhydro-3-(2,3-o-isopropylidene-?-D-ribofuranosyl)-4-hydroxyhexahydropyrimidine-2-thione and its conversions in dilute acetic acid
  作者：A. D. Shutalev、L. A. Ignatova、B. V. Unkovskii

  DOI：10.1007/bf00515085

  日期：1985.6
• N-glycosides. V. 3-glycosyl-4-hydroxyhexahydropyrimidine-2-thiones and their acyclic glycosylthiourea precursors as stimulators of non-specific resistance to infection
  作者：L. A. Ignatova、A. D. Shutalev、B. V. Unkovskii、N. G. Sinilova、A. P. Duplishcheva

  DOI：10.1007/bf01148382

  日期：1985.12
• New Pyrimidine Cyclonucleosides with Hydrogenated Aglycones: Synthesis and X-Ray Structures
  作者：Anatoly D. Shutalev、Valeriy E. Zavodnik、Galina V. Gurskaya

  DOI：10.1080/15257770008045464

  日期：2000.10

  Acid catalysed transformations of (6S)-6,5'-anhydro-6-hydroxy-1-(2',3'-O-isopropylidene-beta -D-ribofuranosyl)hexahydropyrimidine-2-thione are studied. (6R)-6,2'-anhydro-6-hydroxy-1-(alpha -D-ribofuranosyl)hexahydropyrimidine-2-thione was formed as a thermodynamically stable product. Two intermediates, (6S)-6,5'-anhydro-6-hydroxy-1-(beta -D-ribofuranosyl)hexahydropyrimidine-2-thione and 6-hydroxy-1-(D-ribosyl)hexahydropyrimidine-2-thione and products of cleavage of glycosidic bond were identified in the reaction mixtures. Results of X-ray structural determination of the synthesised nucleosides are presented.