phenyl 2,3-dideoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-glycero-pentofuranoside

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 2,3-dideoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-glycero-pentofuranoside
• 英文别名: 4-methoxy-2-[[(2S)-5-phenylsulfanyloxolan-2-yl]methoxy]pyrimidine
• 化学式: C₁₆H₁₈N₂O₃S
• 分子量: 318.397
• InChiKey: IPGZPWMBXVDIKA-SFVWDYPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-dideoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-glycero-pentofuranoside 在 sodium hydroxide 、 dimethyl(methylthio)sulfonium tetrafluoroborate 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.5h， 生成 2,3-二脱氧胞啶
  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-甲氧基嘧啶 、 phenyl 2,3-dideoxy-1-thio-D-glycero-pentofuranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到phenyl 2,3-dideoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-glycero-pentofuranoside
  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

• 5-O-pyrimidyl-2,3-dideoxy-1-thiofuranoside derivative, and production
  申请人：The Noguchi Institute

  公开号：US05811540A1

  公开（公告）日：1998-09-22

  Disclosed is a 5-O-pyrimidyl-2,3-dideoxy-1-thio-D-furanoside derivative represented by the following formula (I) or an L-form isomer thereof: ##STR1## wherein X represents a hydrogen atom, a fluorine atom or an azido group; R.sup.1 represents a C.sub.1-4 alkyl group; R.sup.2 represents a hydrogen atom, a methyl group or a fluorine atom or a trifluoromethyl group; R.sup.3 represents a C.sub.1-10 alkyl group or a C.sub.6-15 aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a chlorine atom, a bromine atom, a methyl group, an ethyl group and a nitro group. When this derivative is reacted with a sulfonium ion-generating reagent to thereby effect an intramolecular N-glycosylation of the derivative, a .beta.-2',3'-dideoxynucleoside derivative which is useful as a precursor of an antiviral agent, such as AZT, DDC or FLT, can be produced with an extremely high stereoselectivity for the .beta.-anomer and in high yield while very little or none of the .alpha.-form isomer corresponding thereto is produced.

  本发明涉及一种5-O-嘧啶基-2,3-二去氧-1-硫代-D-呋喃糖衍生物，其由以下公式（I）或其L-型异构体表示：##STR1## 其中X表示氢原子，氟原子或偶氮基；R1表示C1-4烷基；R2表示氢原子，甲基或氟原子或三氟甲基基团；R3表示C1-10烷基或C6-15芳基，该芳基未取代或被至少一种取代基所取代，所述取代基选自氯原子，溴原子，甲基，乙基和硝基等基团。当该衍生物与产生磺离子的试剂反应以实现衍生物的分子内N-糖基化时，可以高度立体选择性地制备出β-2'，3'-二去氧核苷衍生物，该衍生物可用作抗病毒剂的前体，例如AZT，DDC或FLT，同时高产率地制得，而几乎不产生相应的α-型异构体。
• US5811540A
  申请人：——

  公开号：US5811540A

  公开（公告）日：1998-09-22
• 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.