Di-O-benzoyl-3',5' β-D-xylofurannosyl-9 adenine | 83373-06-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Di-O-benzoyl-3',5' β-D-xylofurannosyl-9 adenine
• 英文别名: 3',5'-di-O-benzoyl-9-β-D-xylofuranosyladenine；9-(3,5-di-O-benzoyl-β-D-xylofuranosyl)adenine；[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-benzoyloxy-4-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 83373-06-2
• 化学式: C₂₄H₂₁N₅O₆
• 分子量: 475.461
• InChiKey: VLGGKCRTGSWDEX-NSAZKJPHSA-N

物化性质

• 沸点：
  747.7±70.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  10

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Di-O-benzoyl-3',5' O-t-butyldimethylsilyl-2' β-D-xylofurannosyl-9 adenine	83373-07-3	C30H35N5O6Si	589.723
  ——	N6-benzoyl-9-(2,3-di-O-benzoyl-β-D-xylofuranosyl)adenine	31079-98-8	C31H25N5O7	579.569
  ——	9-(β-D-lyxofuranosyl)adenine	4005-33-8	C10H13N5O4	267.244
  ——	N,O-Dibenzoyl-6,3' O-monomethoxytrityl-5' β-D-xylofurannosyl-9 adenine	81352-48-9	C44H37N5O7	747.807
  ——	N6,N6,3'-O,5'-O-tetrabenzoyl-9-β-D-xylofuranosyladenine	127246-69-9	C38H29N5O8	683.677
  ——	O-monomethoxytrityl-5' N,O-tribenzoyl-6,2',3' β-D-xylofurannosyl-9 adenine	31079-97-7	C51H41N5O8	851.915
  ——	N6,5'-O-di(monomethoxytrityl)-9-β-D-lyxofuranosyladenine	127277-92-3	C50H45N5O6	811.937
  ——	9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>adenine	83373-09-5	C36H43N5O5Si	653.853
  ——	3'-deoxydenosine	6998-75-0	C10H13N5O3	251.245
  ——	N,O-Dibenzoyl-6,3' O-monomethoxytrityl-5' O-t-butyldimethylsilyl-2' β-D-xylofurannosyl-9 adenine	83373-10-8	C50H51N5O7Si	862.07

反应信息

• 作为反应物：
  描述：

  Di-O-benzoyl-3',5' β-D-xylofurannosyl-9 adenine 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium methylate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.5h， 生成 N,O-Dibenzoyl-6,3' O-monomethoxytrityl-5' β-D-xylofurannosyl-9 adenine
  参考文献：
  名称：

  Gosselin, Gilles; Imbach, Jean-Louis, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 597 - 602

  摘要：

  DOI：
• 作为产物：
  描述：

  Di-O-benzoyl-3',5' O-acetyl-2' β-xylofurannosyl-9 adenine 在 吡啶 、 一水合肼 、 溶剂黄146 作用下， 反应 20.0h， 以82%的产率得到Di-O-benzoyl-3',5' β-D-xylofurannosyl-9 adenine
  参考文献：
  名称：

  Gosselin, Gilles; Imbach, Jean-Louis, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 597 - 602

  摘要：

  DOI：

文献信息

• Reaction of adenine nucleosides, tosylated in the carbohydrate moiety, with lithium triethylborohydride
  作者：Piet Herdewijn

  DOI：10.1016/s0040-4020(01)89533-8

  日期：1989.1

  The reaction of lithium triethylborohydride with the 2′,3′-di-O-p-tolyl-sulphonyl derivatives of 9-/bg-D-ribofuranosyladenine, 9-β-D-arabinofuranosyl-adenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied. The reaction of 2′,3′-di-O-p-tolysulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D--pentofuranosyl)adenine. This rearrangement reaction was used for the synthesis of 9-(3

  三乙基硼氢化锂与9- / bg-D-D-呋喃核糖基腺嘌呤，9-β-D-阿拉伯呋喃糖基腺嘌呤，9-β-D-木呋喃基腺嘌呤和9的2'，3'-二-Op-甲苯基-磺酰基衍生物的反应研究了-β-D-呋喃呋喃糖基腺嘌呤。2′，3′-二-Op-甲苯磺酰腺苷与LiEt 3 BH的反应得到9-（3-脱氧-β-D-戊呋喃糖基）腺嘌呤。该重排反应用于从2'，3'，5'-三-Op-甲苯磺酰赖氨酸腺苷一步合成9-（3,5-二脱氧-β-D-戊呋喃糖基）腺嘌呤，产率为58％。
• Methods of treating hepatitis delta virus infection with beta-l-2'-deoxy-nucleosides
  申请人：——

  公开号：US20020035085A1

  公开（公告）日：2002-03-21

  A method and composition for treating a host infected with hepatitis D comprising administering an effective hepatitis D treatment amount of a described 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof.

  一种治疗感染乙型肝炎的宿主的方法和组合物，包括给予所述2'-脱氧-β-L-赤霉糖核苷或其药用可接受的盐或前药的有效乙型肝炎治疗剂量。
• Beta-L-2'-deoxy-nucleosides for the treatment of hepatitis B
  申请人：Centre National da la Reserche Scientifique

  公开号：US20030220290A1

  公开（公告）日：2003-11-27

  This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside has the formula: 1 wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.

  本发明涉及一种治疗乙型肝炎感染宿主的方法，包括给予一种抗HBV生物活性2'-脱氧-β-L-核糖呋喃核苷或其药学上可接受的盐或前药的有效量，其中2'-脱氧-β-L-核糖呋喃核苷的化学式为：1，其中R选自H、直链、支链或环烷基、CO-烷基、CO-芳基、CO-烷氧基烷基、CO-芳氧基烷基、CO-取代芳基、烷基磺酰基、芳基磺酰基、芳基烷基磺酰基、氨基酸残基、单、二或三磷酸盐或磷酸衍生物；BASE是嘌呤或嘧啶碱基，可以选择性地被取代。2'-脱氧-β-L-核糖呋喃核苷或其药学上可接受的盐或前药可以单独使用或与另一种2'-脱氧-β-L-核糖呋喃核苷或另一种抗乙型肝炎药物联合使用。
• Beta-L-2'deoxy-nucleosides for the treatment of hepatitis B
  申请人：——

  公开号：US20030225028A1

  公开（公告）日：2003-12-04

  This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside has the formula: 1 wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2′-deoxy-&bgr;-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.

  本发明涉及一种治疗乙型肝炎感染宿主的方法，包括给予一种抗HBV生物活性的2'-去氧-&bgr;-L-核糖核苷或其药用盐或前药的有效量，其中2'-去氧-&bgr;-L-核糖核苷具有以下公式：1其中R选自H、直链、支链或环烷基、CO-烷基、CO-芳基、CO-烷氧基烷基、CO-芳氧基烷基、CO-取代芳基、烷基磺酰基、芳基磺酰基、芳基烷基磺酰基、氨基酸残基、单、二或三磷酸盐或磷酸衍生物；BASE是一种可以选择性地取代的嘌呤或嘧啶碱基。2'-去氧-&bgr;-L-核糖核苷或其药用盐或前药可以单独或与另一种2'-去氧-&bgr;-L-核糖核苷或其他抗乙型肝炎药物联合使用。
• beta-L-2'-deoxy-nucleosides for the treatment of hepatitis B
  申请人：Gosselin Gilles

  公开号：US20060084624A1

  公开（公告）日：2006-04-20

  This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2′-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2′-deoxy-β-L-erythro-pentofuranonucleoside has the formula: wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2′-deoxy-β-L-eythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2′-deoxy-β-L-erythro pentofuranonucleoside or in combination with another anti-hepatitis B agent.

  本发明涉及一种治疗乙型肝炎感染宿主的方法，包括给予一种抗HBV生物活性2'-脱氧-β-L-erythro-戊糖核苷或其药学可接受的盐或前药的有效量，其中2'-脱氧-β-L-erythro-戊糖核苷的化学式为：其中R选自H、直链、支链或环烷基、CO-烷基、CO-芳基、CO-烷氧基烷基、CO-芳氧基烷基、CO-取代芳基、烷基磺酰基、芳基磺酰基、芳基烷基磺酰基、氨基酸残基、单磷酸、二磷酸或三磷酸，或磷酸衍生物；BASE是一种可以选择性地被取代的嘌呤或嘧啶碱基。2'-脱氧-β-L-erythro-戊糖核苷或其药学可接受的盐或前药可以单独或与另一种2'-脱氧-β-L-erythro-戊糖核苷或另一种抗乙型肝炎药物联合给予。