2-[(E)-4-[(4-bromophenyl)methoxy]-2,3,4,4-tetradeuteriobut-2-enoxy]oxane | 146668-87-3

• 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: 2-[(E)-4-[(4-bromophenyl)methoxy]-2,3,4,4-tetradeuteriobut-2-enoxy]oxane
• CAS: 146668-87-3
• 化学式: C₁₆H₂₁BrO₃
• 分子量: 345.213
• InChiKey: SRESUWYDVUMBQJ-AQPJHOHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl 4-tetrahydropyranyloxy-2-butinoate 在 lithium aluminium deuteride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-[(E)-4-[(4-bromophenyl)methoxy]-2,3,4,4-tetradeuteriobut-2-enoxy]oxane
  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

文献信息

• A practical synthesis of perdeuterated deoxyribose and deoxyribonucleosides
  作者：Brad K. Goering、Kwangjin Lee、Byungjae An、Jin K. Cha

  DOI：10.1021/jo00057a022

  日期：1993.2

  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).