3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-erythro-pentofuran-1-one-2,2',3,4,5,5'-d6 | 146668-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-erythro-pentofuran-1-one-2,2',3,4,5,5'-d6
• 英文别名: (4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxy-dideuteriomethyl]-3,3,4,5-tetradeuteriooxolan-2-one
• CAS: 146668-81-7
• 化学式: C₁₇H₃₆O₄Si₂
• 分子量: 366.594
• InChiKey: DCFHRVSQGCDCMH-PJLOPVMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-erythro-pentofuran-1-one-2,2',3,4,5,5'-d6 在 DIBAL-D 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 生成
  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：

  5-O-p-bromobenzyl-2-deoxy-D-erythro-pentafuran-1-one-2,2',3,4,5,5'-d6 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-erythro-pentofuran-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