1-(2-O-acetyl-β-D-arabinofuranosyl)-uracil | 169886-74-2

• 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: 1-(2-O-acetyl-β-D-arabinofuranosyl)-uracil
• 英文别名: 2'-O-acetyl-1-β-D-arabinofuranosyluracil；[(2R,3S,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 169886-74-2
• 化学式: C₁₁H₁₄N₂O₇
• 分子量: 286.241
• InChiKey: MCQDRSXCGLYGLH-SFKDOBOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-O-acetyl-β-D-arabinofuranosyl)-uracil 在 咪唑 、 三乙胺 、 三氯化磷 作用下， 生成 1-(2-O-acetyl-5-O-monomethoxytrityl-β-D-arabinofuranosyl)-uracil 3'-O-hydrogenphosphonate
  参考文献：
  名称：

  Building Blocks for Synthesis of Oligoarabinonucleotides: Preparation of Arabinonucleoside H-Phosphonates from Protected Ribonucleosides

  摘要：

  A straightforward and inexpensive synthesis of arabinonucleoside H-phosphonates has been developed. Arabinonucleosides were synthesised from protected ribonucleosides via 2'-keto derivatives. Reaction conditions have been optimised for compounds bearing labile N-protections. Further protecting group manipulation and phosphonylation gave the required H-phosphonate monomers.

  DOI：

  10.1080/15257779508010720
• 作为产物：
  描述：

  [(6aR,8R,9S,9aR)-8-(2,4-dioxopyrimidin-1-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] acetate 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以89%的产率得到1-(2-O-acetyl-β-D-arabinofuranosyl)-uracil
  参考文献：
  名称：

  Building Blocks for Synthesis of Oligoarabinonucleotides: Preparation of Arabinonucleoside H-Phosphonates from Protected Ribonucleosides

  摘要：

  A straightforward and inexpensive synthesis of arabinonucleoside H-phosphonates has been developed. Arabinonucleosides were synthesised from protected ribonucleosides via 2'-keto derivatives. Reaction conditions have been optimised for compounds bearing labile N-protections. Further protecting group manipulation and phosphonylation gave the required H-phosphonate monomers.

  DOI：

  10.1080/15257779508010720

文献信息

• Facile access to 2′-O-acyl prodrugs of 1- (β-d-arabinofuranosyl)-5(E)-(2-bromovinyl)uracil (BVAraU) via regioselective esterase-catalyzed hydrolysis of 2′ 3′, 5′-triesters1
  作者：Pier G. Baraldi、Rita Bazzanini、Stefano Manfredini、Daniele Simoni、Morris J. Robins

  DOI：10.1016/s0040-4039(00)93411-7

  日期：1993.5

  3,5-tri-O-acetyl-β-d-arabinofuranosyl) -5-[2-(trimethylsilyl)-vinyl]uracil (3) with pyridinium bromide perbromide and deacetylation gave BVAraU (2). Pig liver esterase (EC 3.1.1.1) catalysed the regioselective hydrolysis of 1-(2,3,5-tri-O-acyl-β-d-arabinofuranosyl)uracil derivatives to their 2′-O-acyl monoesters.

  用溴化吡啶鎓过溴化物处理1-（2,3,5-三-O-乙酰基-β-d-阿拉伯呋喃糖基）-5- [2-（三甲基甲硅烷基）-乙烯基]尿嘧啶（3）并脱乙酰化得到BVAraU（2） 。猪肝酯酶（EC 3.1.1.1）催化1-（2,3,5-三-O-酰基-β-d-阿拉伯呋喃糖基）尿嘧啶衍生物的区域选择性水解为2'- O-酰基单酯。
• Enzymatic regioselective and complete deacetylation of two arabinonucleosides
  作者：María B. Sabaini、María A. Zinni、Martina Mohorčič、Jožefa Friedrich、Adolfo M. Iribarren、Luis E. Iglesias

  DOI：10.1016/j.molcatb.2009.10.011

  日期：2010.3

  Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2',3',5'-tri-O-acetyl-1-beta-D-arabinofuranosyluracil (1) and 2',3',5'-tri-O-acetyl-9-beta-D-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing different degree of acetylation: in isopropanol, CAL-B catalysed the formation of the corresponding 2'-O-acetylated arabinonucleosides, while hydrolyses afforded the 2',3'-di-O-acetylated products. In particular, the procedure herein described allows a simple and efficient preparation of the reported vidarabine prodrug 2',3'-di-O-acetyl-9-beta-D-arabinofuranosyladenine avoiding the utilisation of protective groups. Moreover, to achieve full deacetylation of the assayed substrates, a set of commercial hydrolases and fungal keratinases from Doratomyces microsporus (DMK) and Paecilomyces marquandii (PMK) were tested. While only PMK and DMK catalysed the quantitative complete deacetylation of 1, DMK accomplished full deacetylation of 2 in shorter time than the other assayed enzymes. (C) 2009 Elsevier B.V. All rights reserved.
• Synthesis of Oligoarabinonucleotides Using H-Phosphonates
  作者：Eriks Rozners、Roger Strömberg、Erika Bizdena

  DOI：10.1080/15257779508012487

  日期：1995.5.1

  Protected arabinonucleoside H-phosphonates have been prepared starting from ribonucleosides and used in solid phase synthesis of oligoarabinonucleotides.
• [EN] COMPOSITIONS FOR EDITING MECP2 TRANSCRIPTS AND METHODS THEREOF<br/>[FR] COMPOSITIONS POUR L'ÉDITION DE TRANSCRITS MECP2 ET PROCÉDÉS ASSOCIÉS
  申请人：[en]WAVE LIFE SCIENCES LTD.

  公开号：WO2023049477A2

  公开（公告）日：2023-03-30

  Among other things, the present disclosure provides oligonucleotides, compositions and methods thereof that can bring about specific editing of a target adenosine in a target RNA molecule. Such oligonucleotides, compositions and methods are useful to treat, prevent, or ameliorate MECP2 associated disorders, diseases and syndromes that can benefit from adenosine modification.