(2R,3R)-3-<<(p-bromobenzyl)oxy>dideuteriomethyl>oxiranemethanol-2,3-d2 | 146668-78-2

• 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: (2R,3R)-3-<<(p-bromobenzyl)oxy>dideuteriomethyl>oxiranemethanol-2,3-d2
• 英文别名: [(2R,3R)-3-[(4-bromophenyl)methoxy-dideuteriomethyl]-2,3-dideuteriooxiran-2-yl]methanol
• CAS: 146668-78-2
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 277.095
• InChiKey: PECBWSBCNVSTRY-KIFACMIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-[(E)-4-[(4-bromophenyl)methoxy]-2,3,4,4-tetradeuteriobut-2-enoxy]oxane 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4 A molecular sieve 、 4-甲基苯磺酸吡啶 、 D-(-)-酒石酸二异丙酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2R,3R)-3-<<(p-bromobenzyl)oxy>dideuteriomethyl>oxiranemethanol-2,3-d2
  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