Acetic acid (2R,3S,4R,5R)-2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester | 786624-54-2

• 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: Acetic acid (2R,3S,4R,5R)-2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester
• CAS: 786624-54-2
• 化学式: C₁₁H₁₅N₃O₆
• 分子量: 285.257
• InChiKey: XCDAMHAMUJBACP-SFKDOBOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.99
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  136.9
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R)-2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester 、 4-甲氧基三苯基氯甲烷 生成 1-(2-O-acetyl-5-O-monomethoxytrityl-β-D-arabinofuranosyl)-N4-isobuturylcytosine
  参考文献：
  名称：

  Synthesis of Oligoarabinonucleotides Using H-Phosphonates

  摘要：

  Protected arabinonucleoside H-phosphonates have been prepared starting from ribonucleosides and used in solid phase synthesis of oligoarabinonucleotides.

  DOI：

  10.1080/15257779508012487
• 作为产物：
  描述：

  Acetic acid (2R,3S,3aR,9aR)-2-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 生成 Acetic acid (2R,3S,4R,5R)-2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of Oligoarabinonucleotides Using H-Phosphonates

  摘要：

  Protected arabinonucleoside H-phosphonates have been prepared starting from ribonucleosides and used in solid phase synthesis of oligoarabinonucleotides.

  DOI：

  10.1080/15257779508012487

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。