[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6-methyl-2-methylsulfanyl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate | 944317-12-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6-methyl-2-methylsulfanyl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 944317-12-8
• 化学式: C₃₂H₂₈N₂O₈S
• 分子量: 600.649
• InChiKey: KHCXDZBLDQBBPN-YULOIDQLSA-N

物化性质

• 沸点：
  726.6±70.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6-methyl-2-methylsulfanyl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate 在 氨 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 6-甲基尿苷
  参考文献：
  名称：

  Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues

  摘要：

  Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (ABR) afforded the corresponding N-1-2,6-disubstituted nucleosides (2a,b) without any trace of the N-3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N-1-6-methyluridine (4) and the corresponding N-1-2-amino-6-metyhl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown.

  DOI：

  10.3987/com-06-s(k)3
• 作为产物：
  描述：

  6-甲基-4-羟基-2-甲硫基嘧啶 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 生成 [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6-methyl-2-methylsulfanyl-4-oxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues

  摘要：

  Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (ABR) afforded the corresponding N-1-2,6-disubstituted nucleosides (2a,b) without any trace of the N-3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N-1-6-methyluridine (4) and the corresponding N-1-2-amino-6-metyhl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown.

  DOI：

  10.3987/com-06-s(k)3

文献信息

• [EN] 2-HYDROXYIMINOPYRIMIDINE NUCLEOSIDES AND DERIVITIVES AND ANTIVIRAL USES THERETO<br/>[FR] NUCLÉOSIDES ET DÉRIVÉS DE 2-HYDROXYIMINOPYRIMIDINE ET UTILISATIONS ANTIVIRALES DE CEUX-CI
  申请人：SINCE & TECH DEVELOPMENT FUND AUTHORITY

  公开号：WO2022008025A1

  公开（公告）日：2022-01-13

  Disclosed herein are nucleosides and nucleotides analogs, methods for preparing the same, and methods for treating and/or ameliorating infection caused by a Coronaviridae virus, a Caliciviridae virus, an Orthomyxoviridae virus, a Herpesviridae virus, a Flaviviridae virus, a Filoviridae virus,and a Pneumoviridae virus with one or more nucleoside and nucleotide analogs of formula I. In certain embodiments, compounds and compositions of nucleoside or nucleotide derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents. In certain embodiments, the compounds are according to Formula (I): or a pharmaceutically acceptable salt, solvate, stereoisomeric form, a tautomeric form or polymorphic form thereof, wherein R1, R2, R3, R4, X, and sugar are as described herein.

  本文披露了核苷和核苷酸类似物，制备它们的方法，以及使用一种或多种公式I的核苷和核苷酸类似物治疗和/或改善由冠状病毒科病毒、钙病毒科病毒、流感病毒科病毒、疱疹病毒科病毒、黄病毒科病毒、丝状病毒科病毒和肺病毒科病毒引起的感染的方法。在某些实施例中，披露了核苷或核苷酸衍生物的化合物和组成物，可以单独或与其他抗病毒药物组合给予。在某些实施例中，化合物符合以下公式(I)：或其药用可接受的盐、溶剂化合物、立体异构体形式、互变异构体形式或多形形式，其中R1、R2、R3、R4、X和糖如本文所述。
• Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues
  作者：Marco Radi、Elena Petricci、Federico Corelli、Maurizio Botta

  DOI：10.3987/com-06-s(k)3

  日期：——

  Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (ABR) afforded the corresponding N-1-2,6-disubstituted nucleosides (2a,b) without any trace of the N-3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N-1-6-methyluridine (4) and the corresponding N-1-2-amino-6-metyhl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown.