5-O-p-bromobenzyl-2-deoxy-D-erythro-pentafuran-1-one-2,2',3,4,5,5'-d6 | 146668-80-6

• 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: 5-O-p-bromobenzyl-2-deoxy-D-erythro-pentafuran-1-one-2,2',3,4,5,5'-d6
• 英文别名: (4S,5R)-5-[(4-bromophenyl)methoxy-dideuteriomethyl]-3,3,4,5-tetradeuterio-4-hydroxyoxolan-2-one
• CAS: 146668-80-6
• 化学式: C₁₂H₁₃BrO₄
• 分子量: 307.089
• InChiKey: VEUWQDBCOHLILH-ZMVQPBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 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：

  5-O-p-bromobenzyl-2-deoxy-D-erythro-pentafuran-1-one-2,2',3,4,5,5'-d6 在 吡啶 、 DIBAL-D 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (4S,5R)-5-[(4-bromophenyl)methoxy-dideuteriomethyl]-4-[tert-butyl(dimethyl)silyl]oxy-2,3,3,4,5-pentadeuteriooxolan-2-ol
  参考文献：
  名称：

  A practical synthesis of perdeuterated deoxyribose and deoxyribonucleosides

  摘要：

  A stereoselective synthesis of perdeuterated deoxyribofuranoside (1) has been developed starting from known methyl 4-(2'-tetrahydropyranyloxy)-2-butynoate. The synthetic strategy involved the Sharpless asymmetric epoxidation of alcohol 7, followed by a tandem epoxide isomerization and opening with NaCN. The resulting lactone 4b was then reduced via its TBDMS derivative with Dibal-D and subsequently converted to perdeuterated deoxyribofuranoside (1).

  DOI：

  10.1021/jo00057a022
• 作为产物：
  描述：

  氰化钠 、 (2R,3R)-3-<<(p-bromobenzyl)oxy>dideuteriomethyl>oxiranemethanol-2,3-d2 生成 5-O-p-bromobenzyl-2-deoxy-D-erythro-pentafuran-1-one-2,2',3,4,5,5'-d6
  参考文献：
  名称：

  A practical synthesis of perdeuterated deoxyribose and deoxyribonucleosides

  摘要：

  A stereoselective synthesis of perdeuterated deoxyribofuranoside (1) has been developed starting from known methyl 4-(2'-tetrahydropyranyloxy)-2-butynoate. The synthetic strategy involved the Sharpless asymmetric epoxidation of alcohol 7, followed by a tandem epoxide isomerization and opening with NaCN. The resulting lactone 4b was then reduced via its TBDMS derivative with Dibal-D and subsequently converted to perdeuterated deoxyribofuranoside (1).

  DOI：

  10.1021/jo00057a022