1-(2,3-O-anhydro-4,6-O-(R)-phenylmethylene-β-D-mannopyranosyl) thymine | 679407-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 1-(2,3-O-anhydro-4,6-O-(R)-phenylmethylene-β-D-mannopyranosyl) thymine
• 英文别名: 1-(2,3-O-anhydro-4,6-O-phenylmethylene-β-D-mannopyranosyl) thymine；5-methyl-1-[(1R,2S,4S,5R,7R,10R)-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecan-5-yl]pyrimidine-2,4-dione
• CAS: 679407-35-3
• 化学式: C₁₈H₁₈N₂O₆
• 分子量: 358.351
• InChiKey: HUWMZXNKUWQJNW-DUUYBOGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2,3-O-anhydro-4,6-O-(R)-phenylmethylene-β-D-mannopyranosyl) thymine 在 叠氮化锂 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以83%的产率得到1-((2R,4aR,6R,7S,8S,8aS)-8-Azido-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  A general and efficient route to 3′-deoxy-3′-N-, S-, and C-substituted altropyranosyl thymines from 2′,3′-O-anhydro-mannopyranosylthymine

  摘要：

  An efficient route to 1-(2,3-O-anhydro-4,6-O-phenylmethylene--D-mannopyranosyl) thymine from 1,2,4,6-tetra-O-acetyl-3-O-tosyl-beta-D-glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3'-position by N-, S-, and C-nucleophiles to afford a wide range of new 3-deoxy-3'-substituted altropyranosyl thymines. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.025
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 吡啶 、 sodium hydroxide 、 sodium methylate 、 四氯化锡 、 对甲苯磺酸 、 异丙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.5h， 生成 1-(2,3-O-anhydro-4,6-O-(R)-phenylmethylene-β-D-mannopyranosyl) thymine
  参考文献：
  名称：

  A general and efficient route to 3′-deoxy-3′-N-, S-, and C-substituted altropyranosyl thymines from 2′,3′-O-anhydro-mannopyranosylthymine

  摘要：

  An efficient route to 1-(2,3-O-anhydro-4,6-O-phenylmethylene--D-mannopyranosyl) thymine from 1,2,4,6-tetra-O-acetyl-3-O-tosyl-beta-D-glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3'-position by N-, S-, and C-nucleophiles to afford a wide range of new 3-deoxy-3'-substituted altropyranosyl thymines. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.025

文献信息

• Synthesis and synthetic applications of 1-(3-O-tosyl-β-d-glucopyranosyl) thymines: toward new classes of hexopyranosyl pyrimidines
  作者：Sachin G. Deshpande、Tanmaya Pathak

  DOI：10.1016/j.tetlet.2003.12.153

  日期：2004.3

  1-(2,4,6-Tri-O-acetyl-3-O-tosyl-β-d-glucopyranosyl) thymine has been synthesized by combining thymine with the appropriate carbohydrate. The availability of this key nucleoside made possible the synthesis of 2,2′-O-anhydro-(4,6-O-phenylmethylene-β-d-altropyranosyl) thymine and 1-(2,3-O-anhydro-4,6-O-phenylmethylene-β-d-mannopyranosyl) thymine. A wide range of modified hexopyranosyl nucleosides can

  通过将胸腺嘧啶与适当的碳水化合物结合，合成了1-（2,4,6-三-O-乙酰基-3- O-甲苯磺酰基-β-d-吡喃葡萄糖基）胸腺嘧啶。该键的核苷的可用性成为可能的2,2合成' - Ö -anhydro-（4,6- ø -苯-β-d-altropyranosyl）胸腺嘧啶和1-（2,3- ø -anhydro-4， 6 - O-苯基亚甲基-β-d-甘露吡喃糖基）胸腺嘧啶。从这些官能化的起始原料可以容易地制备多种修饰的己基吡喃糖基核苷。