3'-O-tosyluridine | 69521-36-4

• 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'-O-tosyluridine
• 英文别名: O^3'-(toluene-4-sulfonyl)-uridine；O^3'-(Toluol-4-sulfonyl)-uridin；rUrd-Tos；[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] 4-methylbenzenesulfonate
• CAS: 69521-36-4
• 化学式: C₁₆H₁₈N₂O₈S
• 分子量: 398.394
• InChiKey: RBQSYLJOONFNCY-NMFUWQPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  尿嘧啶核苷 、 对甲苯磺酰氯 生成 3'-O-tosyluridine
  参考文献：
  名称：

  GROUILLER, ANNIER;ESSADIQ, HASSAN;NAJIB, BOUBKER;MOLIERE, PATRICK, SYNTHESIS,(1987) N 12, 1121-1122

  摘要：

  DOI：

文献信息

• Regioselective<i>O</i>-<i>p</i>-Toluenesulfonylation of Nucleosides Under Solid/Liquid Phase-Transfer Conditions
  作者：Annie Grouiller、Hassan Essadiq、Boubker Najib、Patrick Molière

  DOI：10.1055/s-1987-28193

  日期：——

  The regioselective mono-O-p-toluenesulfonylation of nucleosides under phase-transfer conditions in which dibutyltin oxide acts as a base is reported. The selectivity is dependent upon both the solvent and ammonium quaternary salt.

  报告了在相转移条件下，二丁基锡氧化物作为碱的情况下，核苷的区域选择性单-O-对甲苯磺酰化反应。选择性依赖于溶剂和铵季盐。
• Oligonucleotides having chiral phosphorus linkages
  申请人：——

  公开号：US20010008936A1

  公开（公告）日：2001-07-19

  Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN 2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3′ position of a xylonucleotide. The reaction proceeds via inversion at the 3′ position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

  本发明提供了具有高度纯的手性Sp磷酸硫酯、手性Rp磷酸硫酯、手性Sp烷基膦酸酯、手性Rp烷基膦酸酯、手性Sp磷酰胺酸酯、手性Rp磷酰胺酸酯、手性Sp磷酸三酯和手性Rp磷酸三酯键的序列特异性寡核苷酸。新型寡核苷酸通过对木糖核苷酸的3'位置进行立体特异性的SN2亲核攻击制备而成，反应通过在木糖反应物种的3'位置进行反转，从而将磷酸二酯、磷酸硫酯、磷酸胺酯、磷酸三酯或烷基膦酸酯连接的核糖核苷糖基团并入寡核苷酸中。
• Biocatalytic synthesis of aminodeoxy purine N9-beta-D-nucleosides containing 3-amino-3-deoxy-beta-D-ribofuranose, 3-amino-2,3-dideoxy-beta-D-ribofuranose, and 2-amino-2-deoxy-beta-D-ribofuranose as sugar moieties
  申请人：Barai N. Vladimir

  公开号：US20070065922A1

  公开（公告）日：2007-03-22

  Purine N 9 -β-D-nucleosides containing 3-amino-3-deoxy-β-D-ribofaranose, 3-amino-2,3-dideoxy-β-D-ribofuranose, and 2-amino-2-deoxy-β-D-ribofuranose as sugar moieties are synthesized by biocatalytic transglycosylation of purine bases and the respective 3′-amino-3′-deoxyuridine, 3′-amino-3′-deoxythymidine and 2′-amino-2′-deoxyuridine as donors of the carbohydrate moiety, and the cells of Escherichia coli as a biocatalyst or glutaraldehyde (GA) treated cells of Escherichia coli as a biocatalyst or a mixture of thymidine (uridine) phosphorylase and purine nucleoside phosphorylase.

  含有3-氨基-3-脱氧-β-D-核糖呋喃糖，3-氨基-2,3-二脱氧-β-D-核糖呋喃糖和2-氨基-2-脱氧-β-D-核糖呋喃糖作为糖基团的嘌呤N9-β-D-核苷酸，通过生物催化转基因嘌呤碱基和相应的3'-氨基-3'-脱氧尿苷、3'-氨基-3'-脱氧胸苷和2'-氨基-2'-脱氧尿苷作为碳水化合物基团供体，以大肠杆菌细胞作为生物催化剂或经戊二醛处理的大肠杆菌细胞作为生物催化剂或胸苷（尿苷）磷酸化酶和嘌呤核苷酸磷酸化酶的混合物进行合成。
• Brown et al., Journal of the Chemical Society, 1958, p. 3028,3033
  作者：Brown et al.

  DOI：——

  日期：——
• GROUILLER, ANNIER;ESSADIQ, HASSAN;NAJIB, BOUBKER;MOLIERE, PATRICK, SYNTHESIS,(1987) N 12, 1121-1122
  作者：GROUILLER, ANNIER、ESSADIQ, HASSAN、NAJIB, BOUBKER、MOLIERE, PATRICK

  DOI：——

  日期：——