Cytidylyl-3',5'-adenosine

Base Information

• Chemical Name: Cytidylyl-3',5'-adenosine
• CAS No.: 2382-66-3
• Molecular Formula: C19H25 N8 O11 P
• Molecular Weight: 572.428
• Hs Code.: 29389090
• European Community (EC) Number: 219-187-7
• NSC Number: 91552
• Mol file: 2382-66-3.mol

Synonyms:cytidilyl-3',5'-adenosine;cytidylyl adenosine;cytidylyl-3',5'-adenosine

Chemical Property of Cytidylyl-3',5'-adenosine

Chemical Property:

• Melting Point: 173-175 °C
• Boiling Point: 993.2°Cat760mmHg
• PKA: 1.37±0.50(Predicted)
• Flash Point: 554.5°C
• PSA: 295.48000
• Density: 2.23g/cm³
• LogP: -2.21800
• Storage Temp.: −20°C
• XLogP3: -5.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 572.13804064
• Heavy Atom Count: 39
• Complexity: 1040

Purity/Quality:

97% ^*data from raw suppliers

Adenylyl-3'-5'-cytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1N)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 Cytidylyl-3',5'-adenosine

There total 21 articles about Cytidylyl-3',5'-adenosine 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:

phosphoric acid 5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-tert-butyldisulfanylmethoxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester → phosphoric acid 5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-mercaptomethoxy-tetrahydro-furan-3-yl ester 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester + Cytidin-(3',5')-adenosin (2382-66-3)

Guidance literature:

With DL-dithiothreitol; In phosphate buffer; at 20 ℃; pH=6.0 - 10.0; Further Variations:; Reagents; reaction time; Product distribution;

DOI:10.1021/ja0636587

Reference yield:

2',3'-O,O-bis(t-butyldimethylsilyl)adenosine (69504-15-0) → Cytidin-(3',5')-adenosin (2382-66-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 2,4,6-collidine / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 15 min; 20 deg C, 30 min

2: 70 percent / 2 percent benzenesulfonic acid / CHCl₃; methanol / 2 h / Ambient temperature

3: 1.) t-butylamine, 2.) methanolic ammonia, 3.) TBAF

With 2,4,6-trimethyl-pyridine; tetrabutyl ammonium fluoride; ammonia; tert-butylamine; benzenesulfonic acid; In methanol; chloroform;

Reference yield:

N4-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-O-(4-monomethoxytrityl)cytidine (72409-30-4) → Cytidin-(3',5')-adenosin (2382-66-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 2,4,6-collidine / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 15 min; 20 deg C, 30 min

2: 70 percent / 2 percent benzenesulfonic acid / CHCl₃; methanol / 2 h / Ambient temperature

3: 1.) t-butylamine, 2.) methanolic ammonia, 3.) TBAF

With 2,4,6-trimethyl-pyridine; tetrabutyl ammonium fluoride; ammonia; tert-butylamine; benzenesulfonic acid; In methanol; chloroform;

upstream raw materials:

cytidine 2',3'-cyclic monophosphate

adenosine

C₈₉H₇₅ClN₉O₁₉P

C₄₆H₇₂Cl₃N₈O₁₂PSi₃

Downstream raw materials:

cytidine 2',3'-cyclic monophosphate

cytidine 3'-monophosphate

cytidine-2'-monophosphate

adenosine

Refernces

• 1、 Lu, Jun,Li, Nan-Sheng,Koo, Selene C.,Piccirilli, Joseph A.. "Efficient synthesis of N4-methyl-and N4- hydroxycytidine phosphoramidites". body text. p. 2708 - 2712. Retrieved 2010/10/21.
• 2、 Semenyuk, Andrey,Foeldesi, Andras,Johansson, Tommy,Estmer-Nilsson, Camilla,Blomgren, Peter,Braennvall, Mathias,Kirsebom, Leif A.,Kwiatkowski, Marek. "Synthesis of RNA using 2′-O-DTM protection". . p. 12356 - 12357. Retrieved 2007/10/03.