Adenosine 5',3'-phosphouridine

Base Information

• Chemical Name: Adenosine 5',3'-phosphouridine
• CAS No.: 3256-24-4
• Molecular Formula: C19H24N7O12P
• Molecular Weight: 573.413
• NSC Number: 118092
• Mol file: 3256-24-4.mol

Synonyms:Uridylyladenosine;(3',5')-Uridylyladenosine;Adenosine 5',3'-phosphouridine;Uridine-3',5'-adenosine phosphate;(3'-5')UpA;NSC118092;Uridylyl-(3'.fwdarw.5')-adenosine;NSC-118092;Adenosine, uridylyl-(3'.fwdarw.5')-

Chemical Property of Adenosine 5',3'-phosphouridine

Chemical Property:

• XLogP3: -5.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 8
• Exact Mass: 573.12205622
• Heavy Atom Count: 39
• Complexity: 1030

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)O)O)O

Technology Process of Adenosine 5',3'-phosphouridine

There total 13 articles about Adenosine 5',3'-phosphouridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6-N-benzoyl-2'-O-(tetrahyropyran-2-yl)adenosine (31505-87-0) → phosphoric acid adenosin-5'-yl ester uridin-3'-yl ester (3256-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / cesium fluoride / acetonitrile / Ambient temperature

With cesium fluoride; In acetonitrile;

DOI:10.1246/cl.1980.1419

Reference yield:

5'-O-(dimethoxytrityl)-2'-O-(tetrahydropyranyl)-uridine-3'-(4-chlorophenyl 5-chloro-8-quinolyl-phosphate) (75933-79-8) → phosphoric acid adenosin-5'-yl ester uridin-3'-yl ester (3256-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / cesium fluoride / acetonitrile / Ambient temperature

With cesium fluoride; In acetonitrile;

DOI:10.1246/cl.1980.1419

Reference yield:

5'-dimethoxytrityluridine (81246-79-9) → phosphoric acid adenosin-5'-yl ester uridin-3'-yl ester (3256-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 31 percent / 2,6-lutidine / tetrahydrofuran / 0.33 h / 0 °C

With 2,6-dimethylpyridine; In tetrahydrofuran;

DOI:10.1246/cl.1990.959

upstream raw materials:

C₆₆H₆₆ClN₈O₁₇P

5'-O-dimethoxytrityluridine phosphoromorpholidite

2',3'-di-O-acetyladenosine

6-N-benzoyl-2'-O-(tetrahyropyran-2-yl)adenosine

Downstream raw materials:

uridine 2',3'-cyclic phosphate

uridine-3'-phosphate

uridine 2'-monophosphate

adenosine

Refernces

• 1、 Joshi, Prakash C.,Aldersley, Michael F.,Zagorevskii, Dmitri V.,Ferris, James P.. "A nucleotide dimer synthesis without protecting groups using montmorillonite as catalyst". . p. 536 - 566. Retrieved 2012/10/08.
• 2、 Foeldesi, Andras,Nilson, Frans Peder R.,Glemarec, Corine,Gioeli, Carlo,Chattopadhyaya, Jyoti. "Synthesis of 1'%,2',3',4'%,5',5"-(2)H6-β-D-ribonucleosides and 1'%,2',2",3',4'%,5',5"-(2)H7-β-D-2'-deoxyribonucleosides for Selective Suppression of Proton Resonances in Partially-deuterated Oligo-DNA, Oligo-RNA and in 2,5A core ((1)H-NMR window)". . p. 9033 - 9072. Retrieved 2007/10/02.