7-Deaza-2'-C-methyladenosine

Base Information

• Chemical Name: 7-Deaza-2'-C-methyladenosine
• CAS No.: 443642-29-3
• Deprecated CAS: 1001913-41-2
• Molecular Formula: C12H16 N4 O4
• Molecular Weight: 280.283
• UNII: QRR62J6WEF
• DSSTox Substance ID: DTXSID60963208
• Nikkaji Number: J2.094.208H
• Wikipedia: MK-608
• Wikidata: Q23309937
• ChEMBL ID: CHEMBL236207
• Mol file: 443642-29-3.mol

Synonyms:7-deaza-2'-C-methyladenosine;7-DMA cpd;MK 0608;MK-0608;MK0608

Chemical Property of 7-Deaza-2'-C-methyladenosine

Chemical Property:

• Melting Point: 222 °C(Solv: methanol (67-56-1); acetonitrile (75-05-8))
• Boiling Point: 620.7±55.0 °C(Predicted)
• PKA: 12.51±0.70(Predicted)
• PSA: 126.65000
• Density: 1.75±0.1 g/cm3(Predicted)
• LogP: -0.40370
• Storage Temp.: 2-8°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 280.11715500
• Heavy Atom Count: 20
• Complexity: 373

Purity/Quality:

98%,99%, ^*data from raw suppliers

7-Deaza-2''-C-methyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1N2C=CC3=C(N=CN=C32)N)CO)O)O
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC3=C(N=CN=C32)N)CO)O)O
• Uses: 7-Deaza-2''-C-methyladenosine is a hepatitis C virus (HCV) polymerase inhibitor.

Technology Process of 7-Deaza-2'-C-methyladenosine

There total 22 articles about 7-Deaza-2'-C-methyladenosine 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: 97.0%

4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine (443642-33-9) → 7-deaza-2'-C-methyl-adenosine (443642-29-3)

Guidance literature:

With ammonia; at -78 - 85 ℃; for 24h;

Reference yield:

4-phthalimido-7-[3',5'-di-O-(4-methylbenzoyl)-2'-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine (1053646-61-9) → 7-deaza-2'-C-methyl-adenosine (443642-29-3)

Guidance literature:

With N-butylamine; In methanol; toluene; at 64 ℃;

DOI:10.1021/jo0491096

Reference yield:

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol (168427-35-8) → 7-deaza-2'-C-methyl-adenosine (443642-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 72 h / 20 °C

2.1: 16.7 g / diethyl ether / 7 h / -30 - -15 °C

3.1: HBr; AcOH / CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: NaH / acetonitrile / 4 h / 20 °C

4.2: 5.05 g / acetonitrile / 24 h / 20 °C

5.1: 66 percent / boron trichloride / CH₂Cl₂ / 5.5 h / -78 - -20 °C

6.1: 56 percent / NH₃ / methanol / 14 h / 85 °C

With ammonia; hydrogen bromide; boron trichloride; sodium hydride; Dess-Martin periodane; acetic acid; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm040068f

upstream raw materials:

4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

4-phthalimido-7-[3',5'-di-O-(4-methylbenzoyl)-2'-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

4-amino-7H-pyrrolo[2,3-d]pyrimidine-2-sulfinic acid

2-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)isoindoline-1,3-dione

Downstream raw materials:

4-amino-5-bromo-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-amino-5-chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Refernces

• 1、 -. "NEW ANTIVIRAL MODIFIED NUCLEOSIDES". Page/Page column 82. . Retrieved 2010/04/03.
• 2、 -. "5-nitro-nucleoside compounds for treating viral infections". Page/Page column 17. . Retrieved 2010/11/08.