Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[2-(4-tert-butyl-benzoylamino)-6-oxo-1,6-dihydro-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3-yl ester | 102925-90-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[2-(4-tert-butyl-benzoylamino)-6-oxo-1,6-dihydro-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R,5R)-4-acetyloxy-5-[2-[(4-tert-butylbenzoyl)amino]-6-oxo-3H-purin-9-yl]-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 102925-90-6
• 化学式: C₂₅H₂₉N₅O₈
• 分子量: 527.534
• InChiKey: VRJSQEQLXPIKOT-DYVMYPEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-3',5'-O-(tetraisopropyl-1,3-disiloxane-1,3-diyl)-3'-O-phosphiteamidite 、 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[2-(4-tert-butyl-benzoylamino)-6-oxo-1,6-dihydro-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3-yl ester 在 吡啶 、 四氮唑 、 碘 作用下， 生成 [(2R,3R,4R,5R)-2-[[[(6aR,8R,9R,9aR)-8-(6-benzamidopurin-9-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]oxy-[2-(benzenesulfonyl)ethoxy]phosphoryl]oxymethyl]-4-acetyloxy-5-[2-[(4-tert-butylbenzoyl)amino]-6-oxo-3H-purin-9-yl]oxolan-3-yl] acetate
  参考文献：
  名称：

  Regiospecific synthesis of branched tetranucleotides: U3'p5'A3'p5'U2'p5'G, U3'p5'A3'p5'C2'p5'G, A3'p5'A3'p5'U2'p5'G & A3'p5'A3'p5'C2'p5'G.

  摘要：

  DOI：

  10.1016/s0040-4020(01)86911-8

文献信息

• Synthesis of 1′#,2′,3′,4′#,5′,5″-2H6-β-D-ribonucleosides and 1′#, 2′,2″,3′,4′#,5′,5″-2H7-β-D-2′-deoxyribonucleosides for selective suppression of proton resonances in partially-deuterated oligo-DNA, oligo-RNA and in 2,5A core (1H-NMR window)
  作者：András Földesi、Frans Peder R. Nilson、Corine Glemarec、Carlo Gioeli、Jyoti Chattopadhyaya

  DOI：10.1016/s0040-4020(01)82001-9

  日期：1992.1

  1′#,2′,3′,4′#,5′,5″-2H6-ribonucleosides 13 – 16 were converted in high yields to the corresponding 1′#,2′,2″,3′,4′#,5′,5″-2H7-2′-deoxynucleosides 41 – 44 in the following manner: 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TPDS))-1′#,2′,3′,4#′,5′,5″-2H6-nucleosides 29 – 32 were converted to the corresponding 2′-O-phenoxythiocarbonyl derivatives 33 – 36, which were deoxygenated by tri-n-butyltin

  阮内镍-2 H 2 O在甲基α/β-D-呋喃核糖苷[α/β= 〜3：10] 1的差向异构体混合物上的交换反应产生了甲基1 ＃，2,3,4 ＃，5,5'- 2 H 6 -α/β-呋喃核糖苷2 [在C2，C3，C5 / 5'处为97原子％2 H；C 4（C4 ＃）〜85原子％2 H ；在C1（C1 ＃）]处约20个原子％2 H，以60 – 80％的产率获得，同时还得到了差向异构的木糖和阿拉伯糖副产物。在干燥的吡啶中将粗产物2甲苯磺酸化，并在硅胶柱上小心分离，得到纯的1-O-甲基-2,3,5-三-O-（4-甲苯甲酰基）-α/β-D-1＃，2,3,4 ＃，5,5'- 2 H 6-核呋喃糖苷4（48％）。4转化为1-O-乙酰基-2,3,5-三-O-甲苯甲酰基-α/β-D-1 ＃，2,3,4 ＃，5,5'- 2 H 6-核呋喃糖苷6（ 82％的人提供了合成氘核糖核苷用于RNA或DNA合成的关键组成部分。然后将化合物6与甲硅烷基尿嘧啶，N
• New regiospecific synthesis of the “branched” tri-, penta- & hepta-ribonucleic acids which are formed as the “lariat” in the pre-mRNA processing reactions[Splicing]
  作者：X-. Zhou、G. Remaud、J. Chattopadhyaya

  DOI：10.1016/s0040-4020(01)89837-9

  日期：——

  Synthesis of branched triribonucleotides 14 & 19, branched pentaribonucleotides 37 & 38 and branched heptaribonucleotide 41 are reported using the key intermediate 7 or 9. The advantage of using 7 or 9 is that they circumvent the need for complementary protecting groups for the 2'-hydroxyl functions and for the internucleotidyl phosphodiesters in order to introduce the second phosphodiester bond specifically

  使用关键中间体7或9报告了支链三核糖核苷酸14和19，支链五核糖核苷酸37和38和支链七核糖核苷酸41的合成。使用7或9的优点是它们避免了对于2'-羟基官能团和核苷酸间磷酸二酯的互补保护基的需要，以便特别地在分支点引入第二磷酸二酯键。所有支化的核糖核苷酸14，19，37，38和411 H-和31 P-NMR光谱已明确表征。
• ZHOU, X. -X.;NYILAS, A.;CHATTOPADHYAYA, J., 7TH SYMP. CHEM. NUCL. ACID COMPON., BECHYNE CASTLE, AUG. 30TH - SEPT. 5TH+
  作者：ZHOU, X. -X.、NYILAS, A.、CHATTOPADHYAYA, J.

  DOI：——

  日期：——
• ZHOU, X. -X.;NYILAS, A.;REMAUD, G.;CHATTOPADHYAYA, J., TETRAHEDRON, 43,(1987) N 20, 4685-4698
  作者：ZHOU, X. -X.、NYILAS, A.、REMAUD, G.、CHATTOPADHYAYA, J.

  DOI：——

  日期：——