O(6)-Benzyl-2'-deoxyguanosine

Base Information

• Chemical Name: O(6)-Benzyl-2'-deoxyguanosine
• CAS No.: 129732-90-7
• Molecular Formula: C17H19 N5 O4
• Molecular Weight: 357.369
• DSSTox Substance ID: DTXSID00926478
• Nikkaji Number: J525.747F
• ChEMBL ID: CHEMBL244316
• Mol file: 129732-90-7.mol

Synonyms:O(6)-benzyl-2'-deoxyguanosine;O6-B-dG

Chemical Property of O(6)-Benzyl-2'-deoxyguanosine

Chemical Property:

• Melting Point: 49-52°C
• Boiling Point: 724oC at 760 mmHg
• Flash Point: 391.7oC
• PSA: 129.27000
• Density: 1.61g/cm3
• LogP: 0.55830
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 357.14370410
• Heavy Atom Count: 26
• Complexity: 466

Purity/Quality:

97% ^*data from raw suppliers

O6-Benzyl-2''-deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C2N=C(N=C3OCC4=CC=CC=C4)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(N=C3OCC4=CC=CC=C4)N)CO)O
• Uses: Protected Deoxyguanosine.

Technology Process of O(6)-Benzyl-2'-deoxyguanosine

There total 10 articles about O(6)-Benzyl-2'-deoxyguanosine 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: 84.0%

N-[6-Benzyloxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-acetamide (160363-14-4) → O6-Benzyl-2'-deoxyguanosine (129732-90-7)

Guidance literature:

With sodium hydroxide; In pyridine; at 30 ℃; for 2h;

DOI:10.1021/jm960881d

Reference yield: 45.0%

benzyl bromide (100-39-0) + 2'-Deoxyguanosine (961-07-9) → O6-Benzyl-2'-deoxyguanosine (129732-90-7) + 2-amino-3,9-dihydro-3-(phenylmethyl)-6H-purin-6-one (28741-78-8) + N2-Benzyl-2'-deoxyguanosine (208597-31-3) + N2,N2-Dibenzyl-2'-deoxyguanosine

Guidance literature:

With sodium hydroxide; In 2,2,2-trifluoroethanol; at 20 ℃; for 72h; Further byproducts given;

DOI:10.1021/tx980012m

Reference yield:

O6-benzyl-N2-[[[[4''-[(β-D-glucopyranuronosyl)oxy]-3''-nitrophenyl]methyl]oxy]carbonyl]-2'-deoxyguanosine monosodium salt → O6-Benzyl-2'-deoxyguanosine (129732-90-7)

Guidance literature:

With water; at 37 ℃; pH=7.2; Kinetics; Phosphate buffered saline (PBS);

upstream raw materials:

3',5'-di-O-acetyl-O⁶-benzyl-2'-deoxyguanosine

N-[6-Benzyloxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-acetamide

benzyl bromide

2'-Deoxyguanosine

Downstream raw materials:

O⁶-benzyl-2-fluoro-2'-deoxyinosine

N²-[1-(3,4-dibenzyloxybenz[a]anthracenyl)]-2'-deoxy-(6-benzyloxy)-guanosine

Refernces

• 1、 -. "BETA-GLUGURONIDASE CLEAVABLE PRODRUGS OF O6-ALKYLGUANINE-DNA ALKYLTRANSFERASE INACTIVATORS". Page/Page column 19; 20. . Retrieved 2010/10/20.
• 2、 Zajc,Lakshman,Sayer,Jerina. "Epoxide and diol epoxide adducts of polycyclic aromatic hydrocarbons at the exocyclic amino group of deoxyguanosine". . p. 3409 - 3412. Retrieved 2007/10/02.