2-[[(2S,3S,5R)-3-azido-5-phenylsulfanyloxolan-2-yl]methoxy]-4-methoxy-5-methylpyrimidine | 155446-90-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[[(2S,3S,5R)-3-azido-5-phenylsulfanyloxolan-2-yl]methoxy]-4-methoxy-5-methylpyrimidine
• CAS: 155446-90-5
• 化学式: C₁₇H₁₉N₅O₃S
• 分子量: 373.436
• InChiKey: ALVSDUJGIAKRHK-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[[(2S,3S,5R)-3-azido-5-phenylsulfanyloxolan-2-yl]methoxy]-4-methoxy-5-methylpyrimidine 在 sodium hydroxide 、 Dowex 50 、 dimethyl(methylthio)sulfonium tetrafluoroborate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 齐多夫定
  参考文献：
  名称：

  Stereocontrolled synthesis of pyrimidine 2′,3′-dideoxy-β-nucleosides by intramolecular glycosylation

  摘要：

  beta-2',3'-Dideoxynucleosides and their 3'-azido and 3'-fluoro substituted derivatives were synthesized in a stereocontrolled manner by th dimethyl(methylthio)sulfonium tetrafluoroborate promoted intramolecular glycosylation of phenyl 2,3-dideoxy-5-O-(2-pyrimidyl)-1-thioglycosides followed by hydrolysis or ammonolysis.

  DOI：

  10.1016/s0040-4039(00)73186-8
• 作为产物：
  描述：

  2-氯-4-甲氧基-5-甲基嘧啶 、 [(2S,3S,5R)-3-azido-5-phenylsulfanyloxolan-2-yl]methanol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到2-[[(2S,3S,5R)-3-azido-5-phenylsulfanyloxolan-2-yl]methoxy]-4-methoxy-5-methylpyrimidine
  参考文献：
  名称：

  Stereocontrolled synthesis of pyrimidine 2′,3′-dideoxy-β-nucleosides by intramolecular glycosylation

  摘要：

  beta-2',3'-Dideoxynucleosides and their 3'-azido and 3'-fluoro substituted derivatives were synthesized in a stereocontrolled manner by th dimethyl(methylthio)sulfonium tetrafluoroborate promoted intramolecular glycosylation of phenyl 2,3-dideoxy-5-O-(2-pyrimidyl)-1-thioglycosides followed by hydrolysis or ammonolysis.

  DOI：

  10.1016/s0040-4039(00)73186-8

文献信息

• Stereocontrolled synthesis of 3′-isomeric β-nucleoside by intramolecular glycosylation
  作者：Keiko Sujino、Hideyuki Sugimura

  DOI：10.1039/c39940002541

  日期：——

  Intramolecular glycosylation of a pyrimidine derivative, which was temporarily connected to a 2,3-unsaturated 1-thiopentofuranoside through an ethereal linkage, led to an unusual 3′-isomeric nucleoside in a stereoselective fashion.

  一种嘧啶衍生物通过乙醚连接暂时与 2,3-unsaturated 1-thiopentofuranoside 连接，通过分子内糖基化，以立体选择性方式产生了一种不寻常的 3â²-异构体核苷。
• Stereocontrolled synthesis of pyrimidine 2′,3′-dideoxy-β-nucleosides by intramolecular glycosylation
  作者：Keiko Sujino、Hideyuki Sugimura

  DOI：10.1016/s0040-4039(00)73186-8

  日期：1994.3

  beta-2',3'-Dideoxynucleosides and their 3'-azido and 3'-fluoro substituted derivatives were synthesized in a stereocontrolled manner by th dimethyl(methylthio)sulfonium tetrafluoroborate promoted intramolecular glycosylation of phenyl 2,3-dideoxy-5-O-(2-pyrimidyl)-1-thioglycosides followed by hydrolysis or ammonolysis.