2,2'-dideuterio-2-deoxyribonolactone | 131132-17-7

• 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: 2,2'-dideuterio-2-deoxyribonolactone
• 英文别名: (4S,5R)-3,3-dideuterio-4-hydroxy-5-(hydroxymethyl)oxolan-2-one
• CAS: 131132-17-7
• 化学式: C₅H₈O₄
• 分子量: 134.1
• InChiKey: YIXDEYPPAGPYDP-PLSSQMRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2'-dideuterio-2-deoxyribonolactone 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 DIBAL-D 、 溶剂黄146 、 silver carbonate 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 14.75h， 生成 1',2',2''-trideuterio-3',5'-di-O-p-toluoylthymidine
  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：

  D-(+)-核糖酸-gamma-内酯 在 氘代甲醇-d 、 重水 、 sodium methylate 作用下， 生成 2,2'-dideuterio-2-deoxyribonolactone
  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

文献信息

• HODGE, RICHARD P.;BRUSH, CHARLES K.;HARRIS, CONSTANCE M.;HARRIS, THOMAS M+, J. ORG. CHEM., 56,(1991) N, C. 1553-1564
  作者：HODGE, RICHARD P.、BRUSH, CHARLES K.、HARRIS, CONSTANCE M.、HARRIS, THOMAS M+

  DOI：——

  日期：——