Adenylyl-(3'-5')-adenosine

Base Information

• Chemical Name: Adenylyl-(3'-5')-adenosine
• CAS No.: 2391-46-0
• Molecular Formula: C₂₀H₂₅N₁₀O₁₀P
• Molecular Weight: 596.453
• European Community (EC) Number: 219-239-9
• DSSTox Substance ID: DTXSID201316197
• Nikkaji Number: J216.036F
• Wikidata: Q76009695
• Mol file: 2391-46-0.mol

Synonyms:adenylyl-(3'-5')-adenosine

Chemical Property of Adenylyl-(3'-5')-adenosine

Chemical Property:

• Boiling Point: 1081.3oC at 760 mmHg
• Flash Point: 607.8oC
• PSA: 304.19000
• Density: 2.32g/cm3
• LogP: -1.63500
• Storage Temp.: Store at 0°C
• XLogP3: -5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 8
• Exact Mass: 596.14927403
• Heavy Atom Count: 41
• Complexity: 980

Purity/Quality:

90%,98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OC4C(OC(C4O)N5C=NC6=C(N=CN=C65)N)CO)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O[C@@H]4[C@H](O[C@H]([C@@H]4O)N5C=NC6=C(N=CN=C65)N)CO)O)O)N

Technology Process of Adenylyl-(3'-5')-adenosine

There total 35 articles about Adenylyl-(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:

3-(acetyloxy)-2,2-bis(ethoxycarbonyl)propyl adenosin-5'-yl 3'-O-(pivaloyloxymethyl)adenosin-2'-yl phosphate (1259402-83-9) → C21H30N5O13P (1281797-14-5) + C21H30N5O13P (1281797-12-3) + C26H35N10O12P (1043591-45-2) + Inosine (58-63-9) + adenyl(3'-5')phophoadenine (2391-46-0,30066-84-3,88054-63-1) + adenylyl(3'-5')phosphoadenine (2273-76-9) + adenosine (58-61-7)

Guidance literature:

With hog liver carboxyesterase; water; sodium chloride; at 37 ℃; for 24h; pH=7.5; HEPES buffer; Enzymatic reaction;

DOI:10.1002/cbdv.201000288

Reference yield:

5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) → adenyl(3'-5')phophoadenine (2391-46-0,30066-84-3,88054-63-1) + adenylyl(3'-5')phosphoadenine (2273-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine / dimethyl sulfoxide; N,N-dimethyl-formamide / 3 h

1.2: 2 h

2.1: Na(+)-montmorillonite / 1 h / 24 °C

2.2: 48 h / 24 °C

With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2012.701787

Reference yield:

adenosine 5'-phosphoroimidazolidate sodium salt (60031-83-6) + adenosine (58-61-7) → adenyl(3'-5')phophoadenine (2391-46-0,30066-84-3,88054-63-1) + adenylyl(3'-5')phosphoadenine (2273-76-9)

Guidance literature:

adenosine; With Na(+)-montmorillonite; at 24 ℃; for 1h;

adenosine 5'-phosphoroimidazolidate sodium salt; at 24 ℃; for 48h;

DOI:10.1080/15257770.2012.701787

upstream raw materials:

2',3'-O-isopropylideneadenylyl-(5',3')-adenosine

N⁶-benzoyl-5'-O-dimethoxytrityladenosine 2',3'-cyclic phosphoromorpholidite

2',3'-di-O-acetyladenosine

O^5'-acetyl-O^2'_,O3'-hydroxyphosphoryl-adenosine

Downstream raw materials:

adenosine monophosphate

adenosine 2'-monophosphate

adenosine

adenosine 2',3'-cyclic monophosphate