(3',5'-di-O-benzyl-2'-desoxy-β-D-threo-pentofuranosyl)thymine | 134953-47-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (3',5'-di-O-benzyl-2'-desoxy-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-(3,5-Di-O-benzyl-2-deoxy-β-D-threo-pentofuranosyl)thymine；1-(3',5'-di-O-benzoyl-2'-deoxy-D-threo-pentofuranosyl)thymine；5-methyl-1-[(2R,4R,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 134953-47-2
• 化学式: C₂₄H₂₆N₂O₅
• 分子量: 422.481
• InChiKey: FLJRCPRZKNSMKG-YPAWHYETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3',5'-di-O-benzyl-2'-desoxy-β-D-threo-pentofuranosyl)thymine 在 palladium on activated charcoal 氢气 作用下， 生成 threothymidine
  参考文献：
  名称：

  Selenium-controlled stereoselective synthesis of 2′-deoxynucleosides from glycals. A formal synthesis of AZT

  摘要：

  2'-Deoxynucleosides have been stereoselectively synthesized starting from glycals, using phenylselenenyl reagents.

  DOI：

  10.1016/s0040-4039(00)73571-4
• 作为产物：
  描述：

  (2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.33h， 生成 (3',5'-di-O-benzyl-2'-desoxy-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Stereoselective Synthesis of 2'-Deoxy-.beta.-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases

  摘要：

  The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-alpha-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (alpha:beta = 1:24-0:1) to afford 2'-deoxy-beta-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields. The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable a form. A subsequent S(N)2 type attack to the intermediate will lead to the beta-nucleosides. By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-beta-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside. On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products. The product distribution of the regioisomers was, however, proved to change with reaction time. For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (alpha:beta = 1:2-1:4.8). The isolated yields of the 9-beta isomers after purification were acceptable for practical use.

  DOI：

  10.1021/jo00104a020

文献信息

• β-Selective synthesis of 2'-deoxynucleosides by the coupling of 2-deoxy-1-thio-D-threo-pentofuranosides with silylated thymine
  作者：Hideyuki Sugimura、Keiko Sujino、Kenji Osumi

  DOI：10.1016/s0040-4039(00)92229-9

  日期：1992.4

  The coupling of the 3,5-O-isopropylidene derivative of phenyl 2-deoxy-1-thio-D-threo-pentofuranoside with silylated thymine in the presence of N-bromosuccinimide yielded 1-(2-deoxy-beta-D-threo-pentofuranosyl)thymine with highly anomeric selectivity.
• Benhaddou, R.; Czernecki, S.; Valery, J. M., Bulletin de la Societe Chimique de France, 1991, # 1, p. 108 - 111
  作者：Benhaddou, R.、Czernecki, S.、Valery, J. M.、Bellosta, V.

  DOI：——

  日期：——
• Antonov, K. V.; Karpeiskii, A. M.; Miroshnikov, A. I., Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 4, p. 236 - 240
  作者：Antonov, K. V.、Karpeiskii, A. M.、Miroshnikov, A. I.

  DOI：——

  日期：——
• BENHADDOU, R.;CZERNECKI, S.;VALERY, J. M.;BELLOSTA, V., BULL. SOC. CHIM. FR.,(1991) N, C. 108-111
  作者：BENHADDOU, R.、CZERNECKI, S.、VALERY, J. M.、BELLOSTA, V.

  DOI：——

  日期：——
• Stereoselective Synthesis of 2'-Deoxy-.beta.-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases
  作者：Hideyuki Sugimura、Kenji Osumi、Yasuko Kodaka、Keiko Sujino

  DOI：10.1021/jo00104a020

  日期：1994.12

  The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-alpha-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (alpha:beta = 1:24-0:1) to afford 2'-deoxy-beta-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields. The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable a form. A subsequent S(N)2 type attack to the intermediate will lead to the beta-nucleosides. By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-beta-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside. On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products. The product distribution of the regioisomers was, however, proved to change with reaction time. For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (alpha:beta = 1:2-1:4.8). The isolated yields of the 9-beta isomers after purification were acceptable for practical use.