tert-butyldimethylsilyl nitrate | 146668-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: tert-butyldimethylsilyl nitrate
• 英文别名: [tert-butyl(dimethyl)silyl] nitrate
• CAS: 146668-79-3
• 化学式: C₆H₁₅NO₃Si
• 分子量: 177.275
• InChiKey: WNWPPSNPXZNZBG-UHFFFAOYSA-N

物化性质

• 沸点：
  177.5±23.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl nitrate 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 1-deuterio-3,5-di-O-(tert-butyldimethylsilyl)-2-deoxyribose
  参考文献：
  名称：

  Synthesis of 1- and 1,2,2'-deuteriated deoxyribose and incorporation into deoxyribonucleosides

  摘要：

  Thymidine, deoxycytidine, deoxyadenosine, and deoxyguanosine have been prepared with deuterium substitution at position 1' and at position 1', 2', and 2'' from deuteriated deoxyribose. The synthetic strategy involved reduction of the bis(tert-butyldimethylsilyl) derivative 4a of 2-deoxyribonolactone (3a) with Dibal-D followed by deprotection (HCl/MeOH and tetrabutylammonium fluoride) to give 1-deuterio methyl glycoside 7a which was converted to the 1-deuterio 3,5-ditoluoyl methyl glycoside 8a. Preliminary exchange of 2-deoxyribonolactone with NaOMe/MeOD brought about 2,2'-dideuteriation; treatment as above gave the 1,2,2'-trideuterio 3,5-ditoluoyl methyl glycoside 8b. 8a and 8b were condensed with heterocyclic bases via alpha-chloro derivatives 9a and 9b to form deoxynucleosides. New methods were utilized for preparation of deoxycytidine and deoxyguanosine which are improvements over published procedures.

  DOI：

  10.1021/jo00004a040
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyldimethylsilyl nitrate
  参考文献：
  名称：

  Nitrate ion as catalyst for selective silylations of nucleosides

  摘要：

  DOI：

  10.1016/s0040-4039(01)92340-8

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).
• Nitrate ion as catalyst for selective silylations of nucleosides
  作者：Gholam H. Hakimelahi、Zbigniew A. Proba、Kelvin K. Ogilvie

  DOI：10.1016/s0040-4039(01)92340-8

  日期：1981.1
• Synthesis of 1- and 1,2,2'-deuteriated deoxyribose and incorporation into deoxyribonucleosides
  作者：Richard P. Hodge、Charles K. Brush、Constance M. Harris、Thomas M. Harris

  DOI：10.1021/jo00004a040

  日期：1991.2

  Thymidine, deoxycytidine, deoxyadenosine, and deoxyguanosine have been prepared with deuterium substitution at position 1' and at position 1', 2', and 2'' from deuteriated deoxyribose. The synthetic strategy involved reduction of the bis(tert-butyldimethylsilyl) derivative 4a of 2-deoxyribonolactone (3a) with Dibal-D followed by deprotection (HCl/MeOH and tetrabutylammonium fluoride) to give 1-deuterio methyl glycoside 7a which was converted to the 1-deuterio 3,5-ditoluoyl methyl glycoside 8a. Preliminary exchange of 2-deoxyribonolactone with NaOMe/MeOD brought about 2,2'-dideuteriation; treatment as above gave the 1,2,2'-trideuterio 3,5-ditoluoyl methyl glycoside 8b. 8a and 8b were condensed with heterocyclic bases via alpha-chloro derivatives 9a and 9b to form deoxynucleosides. New methods were utilized for preparation of deoxycytidine and deoxyguanosine which are improvements over published procedures.