1β-(6-oxo-1H-pyridin-3-yl)-1-deoxy-D-ribofuranose | 188871-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-(6-oxo-1H-pyridin-3-yl)-1-deoxy-D-ribofuranose
• CAS: 188871-50-3
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.21
• InChiKey: FVBILTKUBHIPQL-QQRDMOCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,5-tri-O-tert-butyldimethylsilyl-D-ribono-1,4-lactone 在 2-二叔丁基膦-3,4,5,6-四甲基-2′,4′,6′-三异丙基-1,1′-联苯 、 三乙基硅烷 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 三氟乙酸 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 6.93h， 生成 1β-(6-oxo-1H-pyridin-3-yl)-1-deoxy-D-ribofuranose
  参考文献：
  名称：

  General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups

  摘要：

  A general modular and practical methodology for preparation of diverse 5-substituted pyriclin-2-yl and 6-substituted pyridin-3-yl C-ribonucleosides was developed. Regioselective lithiation of 2,5-dibromopyridine proceeded at position 5 or 2 depending on the solvent, and the resulting bromopyridyl lithium species underwent additions to TBS-protected ribonolactone and follow-up transformations to corresponding acetylated hemiketal intermediates 7 and 10 that were diastereoselectively reduced to give either 5-bromopyridin-2-yl or 6-bromopyridin3-yl silyl-protected C-ribonucleosides 8 or 11 in 68% and 77% overall yields as pure beta-anomers. These bromopyridyl C-nucleoside intermediates were then subjected to a series of palladium-catalyzed cross-coupling reactions, aminations, aminocarbonylations, and hydroxylations to give a series of protected 1 beta-(5-alkyl-, 5-aryl-, 5-amino-, 5-carbamoyl-, and 5-hydroxypyridin-2-yl)-C-ribonucleosides 13a-i and beta-(6-alkyl-, 6-aryl-, 6-amino-, 6-carbamoyl-, and 6-hydroxypyridin-3-yl)-C-ribonucleosides 15a-i. Deprotection of silylated nucleosides by Et3N center dot 3HF, TBAF, or TFA gave a series of free C-nucleosides 14a-i and 16a-i.

  DOI：

  10.1021/jo200949c

文献信息

• Synthesis of 5-(β-D-ribofuranosyl)-pyridin-2-one: A “deletion-modiffied” analogue of uridine
  作者：Jasenka Matulic-Adamic、Leonid Beigelman

  DOI：10.1016/s0040-4039(97)00197-4

  日期：1997.3

  Pyridin-2-one C-nucleoside2 was prepared using several different approaches. The most efficient pathway utilized the condensation of (4) and 2-(benzyloxy)-5-bromopyridine (5), followed by deoxygenation with and removal of the benzyl protecting groups.

  使用几种不同的方法制备吡啶-2-酮C-核苷2。最有效的途径利用（4）和2-（苄氧基）-5-溴吡啶（5）的缩合，然后用苄基保护基脱氧并除去苄基保护基。
• ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF
  申请人：Moderna Therapeutics, Inc.

  公开号：US20150167017A1

  公开（公告）日：2015-06-18

  The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

  本公开提供了替代核苷、核苷酸和核酸以及它们的使用方法。
• [EN] ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF<br/>[FR] MOLÉCULES D'ACIDE NUCLÉIQUE ALTERNATIVES ET LEURS UTILISATIONS
  申请人：MODERNA THERAPEUTICS INC

  公开号：WO2015196130A3

  公开（公告）日：2016-03-03
• Alternative nucleic acid molecules and uses thereof
  申请人：Moderna Therapeutics, Inc.

  公开号：EP2918275B1

  公开（公告）日：2016-05-18
• CHEMICAL SYNTHESIS OF NUCLEOSIDES ANALOGS AND THEIR INCORPORATION INTO POLYNUCLEOTIDES
  申请人：RIBOZYME PHARMACEUTICALS, INC.

  公开号：EP0948511A2

  公开（公告）日：1999-10-13