2-(Methylsulfanyl)-9-pentofuranosyl-9h-purin-6-amine

Base Information

• Chemical Name: 2-(Methylsulfanyl)-9-pentofuranosyl-9h-purin-6-amine
• CAS No.: 4105-39-9
• Molecular Formula: C11H15N5O4S
• Molecular Weight: 313.337
• NSC Number: 36900
• DSSTox Substance ID: DTXSID50961410
• Mol file: 4105-39-9.mol

Synonyms:2-methylthioadenosine

Chemical Property of 2-(Methylsulfanyl)-9-pentofuranosyl-9h-purin-6-amine

Chemical Property:

• Vapor Pressure: 1.77E-23mmHg at 25°C
• Refractive Index: 1.878
• Boiling Point: 747.6°Cat760mmHg
• Flash Point: 406°C
• PSA: 164.84000
• Density: 1.98g/cm³
• LogP: -0.67690
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 313.08447515
• Heavy Atom Count: 21
• Complexity: 381

Purity/Quality:

97% ^*data from raw suppliers

2-Methylthioadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N

Technology Process of 2-(Methylsulfanyl)-9-pentofuranosyl-9h-purin-6-amine

There total 22 articles about 2-(Methylsulfanyl)-9-pentofuranosyl-9h-purin-6-amine 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: 92.0%

2',3',5'-tri-O-benzoyl-2-(methylthio)adenosine (51549-17-8) → 2-(methylthio)adenosine (4105-39-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/ja028015f

Reference yield: 89.0%

2-Mercaptoadenosine (43157-50-2) + methyl iodide (74-88-4) → 2-(methylthio)adenosine (4105-39-9)

Guidance literature:

2-Mercaptoadenosine; With sodium dithionite; In N,N-dimethyl-formamide; for 0.5h; Inert atmosphere;

With sodium hydroxide; In water; N,N-dimethyl-formamide; for 0.166667h; Cooling with ice;

methyl iodide; In water; N,N-dimethyl-formamide; at 20 ℃; Cooling with ice;

DOI:10.1016/j.ejmech.2015.10.055

Reference yield: 77.0%

2-Chloroadenosine (146-77-0) + carbonic acid dimethyl ester (616-38-6) → 2-(methylthio)adenosine (4105-39-9)

Guidance literature:

With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate; In dimethyl sulfoxide; at 120 ℃; Inert atmosphere;

upstream raw materials:

2-(methylthio)-7H-purin-6-amine

2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride

2-Chloroadenosine

sodium thiomethoxide

Downstream raw materials:

2-methylthioadenosine 5'-monophosphate

N-[[9-(β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester

N-[[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester

N-[[9-(5'-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester