(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile | 117174-40-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: (2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile
• 英文别名: (2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile
• CAS: 117174-40-0
• 化学式: C₂₃H₄₁N₃O₆Si₂
• 分子量: 511.766
• InChiKey: XAKFRKKTOJLDIV-PDPLOHQNSA-N

物化性质

• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  126.57
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile 、 硫代氯甲酸苯酯 生成 (2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-phenoxycarbothioyloxyoxolane-3-carbonitrile
  参考文献：
  名称：

  CALVO-MATEO, ANA;CAMARASA, MARIA-JOSE;DIAZ-ORTIZ, ANGEL;HERAS, FEDERICO G+, TETRAHEDRON, 44,(1988) N 15, C. 4895-4903

  摘要：

  DOI：
• 作为产物：
  描述：

  1-<2,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine 生成 (2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile
  参考文献：
  名称：

  CALVO-MATEO, ANA;CAMARASA, MARIA-JOSE;DIAZ-ORTIZ, ANGEL;HERAS, FEDERICO G+, TETRAHEDRON, 44,(1988) N 15, C. 4895-4903

  摘要：

  DOI：

文献信息

• 3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: synthesis and antiviral activity of [2', 5'-bis-O-(tert-butyldimethylsilyl)-.beta.-D-xylo- and -ribofuranose]-3'-spiro-5''-[4''-amino-1'', 2''-oxathiole 2'', 2''-dioxide] (TSAO) pyrimidine nucleosides
  作者：Maria Jose Camarasa、Maria Jesus Perez-Perez、Ana San-Felix、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00093a002

  日期：1992.7

  A series of 3'-spiro nucleosides have been synthesized and evaluated as anti-HIV-1 agents. Reaction of O-mesylcyanohydrins of furanos-3'-ulosyl nucleosides with base afforded [1-[2',5'-bis-O- (tert-butyldimethylsilyl)-beta-D-xylo- and -ribofuranosyl]]-3'-spiro-5"- [4"-amino-1",2"-oxathiole 2",2"-dioxide] derivatives of thymine, uracil and 4-N-acetylcytosine 11 and 12. Desilylation of 11 and 12 gave

  已经合成了一系列的3'-螺核苷，并被评估为抗HIV-1药物。呋喃糖-3'-核糖基核苷酸的O-甲磺酰基氰醇与碱反应，得到[1- [2'，5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-二甲苯基和-呋喃呋喃糖基]]-3'胸腺嘧啶，尿嘧啶和4-N-乙酰胞嘧啶11和12的-spiro-5“-[4”-氨基-1“，2”-草硫醇2“，2”-二氧化物]衍生物11和12的甲硅烷基化可得到全部去保护的3'-螺木糖核糖核苷酸和核呋喃糖基核苷13和14或部分5'-O-去保护的3'-螺β-D-木糖和核糖核苷15和16，或2'-O-去保护的- 3′-螺β-D-核糖核苷17。17的2′-脱氧得到2′-脱氧-3′-螺β-D-赤型-五呋喃糖基衍生物18。这3′。评价了螺-螺衍生物的抗HIV-1活性。具有木糖构型的所有3'-螺核苷均未显示出任何抗HIV-1活性。在C-2'或C-5'处没有或仅有一个甲硅烷基或2'-脱氧衍生物的