3',5'-O-bis(4-chlorobenzoyl)-2'-deoxy-β-D-uridine | 5173-91-1

• 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: 3',5'-O-bis(4-chlorobenzoyl)-2'-deoxy-β-D-uridine
• 英文别名: O^3'_,O5'-bis-(4-chloro-benzoyl)-2'-deoxy-uridine；3',5'-O-bis(4-chlorobenzoyl)-2'-deoxyuridine；3',5'-Bis-O-(4-chlor-benzoyl)-2'-desoxy-uridin；[(2R,3S,5R)-3-(4-chlorobenzoyl)oxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-chlorobenzoate
• CAS: 5173-91-1
• 化学式: C₂₃H₁₈Cl₂N₂O₇
• 分子量: 505.311
• InChiKey: ZENYRNQJDVPHBS-NLWGTHIKSA-N

物化性质

• 熔点：
  211-212 °C
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3',5'-O-bis(4-chlorobenzoyl)-2'-deoxy-β-D-uridine 在 N-甲基哌啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 生成 2'-脱氧胞嘧啶核苷
  参考文献：
  名称：

  LARGE-SCALE MANUFACTURING OF ALL FOUR 2′-DEOXYNUCLEOSIDES VIA NOVEL STRATEGIES INCLUDING A CHEMO-ENZYMATIC PROCESS

  摘要：

  A chemical synthesis of 2-deoxyribose-1-phosphate 2 and its enzymatic conversion into purine 2'-deoxynucleosides (dNus) are shown. Besides the chemoenzymatic process for purine dNus, a modified process for practical dC preparation is also established. Consequently, a series of practical manufacturing processes of all four dNus have been realized via novel strategies.

  DOI：

  10.1081/ncn-100002539
• 作为产物：
  描述：

  1-氯-2-脱氧-3,5-二-O-对氯苯甲酰基-D-核糖 、 2,4-二(三甲硅氧基)嘧啶 以 氯仿 为溶剂， 反应 3.0h， 以95%的产率得到3',5'-O-bis(4-chlorobenzoyl)-2'-deoxy-β-D-uridine
  参考文献：
  名称：

  An Efficient Amination Method for Manufacturing Cytidines

  摘要：

  A novel method for amination of uridine derivatives was developed and applied to the syntheses of cytidines. The method consists of an activation step with I-methylpiperidine at the C-4-position of a uracil base. Large-scale preparation of 2'-deoxycytidine was performed using this method.

  DOI：

  10.1021/op0499371

文献信息

• Process for the preparation of cytidine derivatives
  申请人：——

  公开号：US20030032797A1

  公开（公告）日：2003-02-13

  An efficient method for producing cytidine derivatives that took away the previous drawbacks by efficiently synthesizing cytidine derivatives by utilizing a tertiary amine can be provided.

  一种高效生产胞嘧啶衍生物的方法，通过利用三级胺有效地合成胞嘧啶衍生物，从而消除了先前的缺点。
• Stereoselective Synthesis of Anomers of 5-Substituted 2′-Deoxyuridines
  作者：Hajime Aoyama

  DOI：10.1246/bcsj.60.2073

  日期：1987.6

  The substitution reaction of 5-substituted 2,4-bis(trimethylsilyloxy)pyrimidines with 3,5-bis(O-p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride was investigated. In the presence of p-nitrophenol, β anomers were formed stereoselectively, whereas the addition of organic bases brought forth stereoselective formation of α anomers. Stereoselectivity of the reaction depends on the substituents at 5-position

  研究了5-取代的2,4-双(三甲基甲硅烷氧基)嘧啶与3,5-双(Op-氯苯甲酰基)-2-脱氧-α-D-呋喃核糖基氯的取代反应。在对硝基苯酚的存在下，β端基异构体立体选择性地形成，而有机碱的加入导致α端基异构体的立体选择性形成。反应的立体选择性取决于二甲硅烷基嘧啶的 5 位取代基、添加剂和每种试剂的浓度。5-取代的2'-脱氧-尿苷的α和β异头通过5-取代3',5'-二-O-(对-氯苯甲酰基)-2'-脱氧尿苷的α和β异头脱酰化合成。
• AOYAMA, HAJIME, BULL. CHEM. SOC. JAP., 60,(1987) N 6, 2073-2077
  作者：AOYAMA, HAJIME

  DOI：——

  日期：——
• Reversible thermochromic composition having improved light-fastness and product comprising same
  申请人：THE PILOT INK CO., LTD.

  公开号：EP1179435B1

  公开（公告）日：2006-11-29
• US6638620B2
  申请人：——

  公开号：US6638620B2

  公开（公告）日：2003-10-28