(2R,3R)-3-<(benzyloxy)methyl>-2,8-dimethyl-2,3-dihydro-5H,9H-pyrimido<2,1-b>-1,5,3-dioxazepin-9-one | 135513-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: (2R,3R)-3-<(benzyloxy)methyl>-2,8-dimethyl-2,3-dihydro-5H,9H-pyrimido<2,1-b>-1,5,3-dioxazepin-9-one
• 英文别名: (2R,3R)-2,8-dimethyl-3-(phenylmethoxymethyl)-3,5-dihydro-2H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one
• CAS: 135513-61-0
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: XHIJUQUZCRBHRV-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-<(benzyloxy)methyl>-2,8-dimethyl-2,3-dihydro-5H,9H-pyrimido<2,1-b>-1,5,3-dioxazepin-9-one 在 palladium on activated charcoal 环己烯 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以42%的产率得到(2R,3R)-2,8-dimethyl-3-(hydroxymethyl)-2,3-dihydro-5H,9H-pyrimido<2,1-b>-1,5,3-dioxazepin-9-one
  参考文献：
  名称：

  1',2'-Secothymidines. The preparation of 2,3'-anhydro derivatives and the formation of two unusual dimeric products

  摘要：

  2,2'- and 2,3'-anhydropyrimidine nucleosides are rigid compounds that are restricted to the syn conformation. In certain cases, this enforced conformational rigidity has led to biologically active compounds. To capitalize on this rationale, attempts were made to prepare the corresponding anhydro analogues of 1',2'-secothymidine. Starting with the functionalized butanetetrols and -triols (1a-c and 2a-c), derived from D-isoascorbic acid, the 1',2'-seco nucleoside tosylates 9a-c were prepared. While attempts to form the 2,3'-anhydro derivatives (10a and 12) were successful, no 2,2'-anhydro analogues could be obtained even under a variety of reaction conditions. Instead, unusual dimeric compounds were formed whose structures were confirmed by C-13 NMR and mass spectrometry. The dimerization reaction does not appear to have been previously reported.

  DOI：

  10.1021/jo00015a017
• 作为产物：
  描述：

  (2R,3S)-3-O-allyl-1-O-benzylbutane-1,2,3-triol 在 palladium on activated charcoal 、 四丁基碘化铵 吡啶 、 盐酸 、 ammonium sulfate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 六甲基二硅氮烷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 60.0h， 生成 (2R,3R)-3-<(benzyloxy)methyl>-2,8-dimethyl-2,3-dihydro-5H,9H-pyrimido<2,1-b>-1,5,3-dioxazepin-9-one
  参考文献：
  名称：

  1',2'-Secothymidines. The preparation of 2,3'-anhydro derivatives and the formation of two unusual dimeric products

  摘要：

  2,2'- and 2,3'-anhydropyrimidine nucleosides are rigid compounds that are restricted to the syn conformation. In certain cases, this enforced conformational rigidity has led to biologically active compounds. To capitalize on this rationale, attempts were made to prepare the corresponding anhydro analogues of 1',2'-secothymidine. Starting with the functionalized butanetetrols and -triols (1a-c and 2a-c), derived from D-isoascorbic acid, the 1',2'-seco nucleoside tosylates 9a-c were prepared. While attempts to form the 2,3'-anhydro derivatives (10a and 12) were successful, no 2,2'-anhydro analogues could be obtained even under a variety of reaction conditions. Instead, unusual dimeric compounds were formed whose structures were confirmed by C-13 NMR and mass spectrometry. The dimerization reaction does not appear to have been previously reported.

  DOI：

  10.1021/jo00015a017

文献信息

• CICHY, ANNE F.;SAIBABA, RACHA;EL, SUBBAGH HUSSEIN I.;PANZICA, RAYMOND P.;+, J. ORG. CHEM., 56,(1991) N5, C. 4653-4658
  作者：CICHY, ANNE F.、SAIBABA, RACHA、EL, SUBBAGH HUSSEIN I.、PANZICA, RAYMOND P.、+

  DOI：——

  日期：——