methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-β-D-erythro-pentofuranoside | 159721-70-7

• 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: methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-β-D-erythro-pentofuranoside
• 英文别名: methyl 3-benzoylthio-5-O-t-butyldiphenylsilyl-2,3-dideoxy-beta-d-erythro-pentofuranoside；S-[(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methoxyoxolan-3-yl] benzenecarbothioate
• CAS: 159721-70-7
• 化学式: C₂₉H₃₄O₄SSi
• 分子量: 506.738
• InChiKey: ORKHGOOBJDAIQC-KWXIBIRDSA-N

物化性质

• 沸点：
  560.5±50.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-β-D-erythro-pentofuranoside 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 sodium methylate 作用下， 以 乙腈 为溶剂， 反应 6.5h， 生成 1-[(2R,4S,5R)-5-(羟基甲基)-4-硫基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Convergent synthesis of 2?,3?-dideoxy-3?-mercapto nucleosides ? Potential anti-HIV agents

  摘要：

  Methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-beta-D- erythro-pentofuranoside (4) and its corresponding alpha anomer 5 were synthesized in four steps from 2-deoxy-D-ribose and used as substrates for the synthesis of nucleosides by condensation with silylated thymidine and N-6-isobutyryladenine. The nucleosides were deprotected by treatment with Bu(4)NF in THF followed by reaction with MeONa in MeOH to give 3'-deoxy-3'-mercaptothymidine (8), 2',3'-dideoxy-3'mercaptoadenosine (15) and its corresponding alpha anomer 16. In the latter reactions it was important to use degassed solvents to minimize formation of the corresponding disulfides of purine nucleosides. Using Bu(4)NF, without subsequent reaction with MeONa in the deprotection reaction, resulted in intermolecular transesterification reactions.

  DOI：

  10.1007/bf00812717
• 作为产物：
  描述：

  methyl 5-O-tert-butyldiphenylsilyl-3-iodo-2,3-dideoxy-β-D-threo-pentofuranoside 、 sodium thiobenzoate 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以80%的产率得到methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-β-D-erythro-pentofuranoside
  参考文献：
  名称：

  Convergent synthesis of 2?,3?-dideoxy-3?-mercapto nucleosides ? Potential anti-HIV agents

  摘要：

  Methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-beta-D- erythro-pentofuranoside (4) and its corresponding alpha anomer 5 were synthesized in four steps from 2-deoxy-D-ribose and used as substrates for the synthesis of nucleosides by condensation with silylated thymidine and N-6-isobutyryladenine. The nucleosides were deprotected by treatment with Bu(4)NF in THF followed by reaction with MeONa in MeOH to give 3'-deoxy-3'-mercaptothymidine (8), 2',3'-dideoxy-3'mercaptoadenosine (15) and its corresponding alpha anomer 16. In the latter reactions it was important to use degassed solvents to minimize formation of the corresponding disulfides of purine nucleosides. Using Bu(4)NF, without subsequent reaction with MeONa in the deprotection reaction, resulted in intermolecular transesterification reactions.

  DOI：

  10.1007/bf00812717

文献信息

• Convergent synthesis of 2?,3?-dideoxy-3?-mercapto nucleosides ? Potential anti-HIV agents
  作者：A. A. El-Barbary、A. I. Khodair、E. B. Pedersen、C. Nielsen

  DOI：10.1007/bf00812717

  日期：——

  Methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-beta-D- erythro-pentofuranoside (4) and its corresponding alpha anomer 5 were synthesized in four steps from 2-deoxy-D-ribose and used as substrates for the synthesis of nucleosides by condensation with silylated thymidine and N-6-isobutyryladenine. The nucleosides were deprotected by treatment with Bu(4)NF in THF followed by reaction with MeONa in MeOH to give 3'-deoxy-3'-mercaptothymidine (8), 2',3'-dideoxy-3'mercaptoadenosine (15) and its corresponding alpha anomer 16. In the latter reactions it was important to use degassed solvents to minimize formation of the corresponding disulfides of purine nucleosides. Using Bu(4)NF, without subsequent reaction with MeONa in the deprotection reaction, resulted in intermolecular transesterification reactions.