alpha-2'-Deoxythioguanosine

Base Information

• Chemical Name: alpha-2'-Deoxythioguanosine
• CAS No.: 789-61-7
• Molecular Formula: C10H13 N5 O3 S
• Molecular Weight: 283.311
• NSC Number: 71851,71261
• DSSTox Substance ID: DTXSID50859540
• ChEMBL ID: CHEMBL1971770
• Mol file: 789-61-7.mol

Synonyms:.alpha.-TGdR;.alpha.-Thiodeoxyguanosine;.alpha.-2'-Deoxythioguanosine;.alpha.-2'-Deoxy-6-thioguanosine;NSC71851;Thioguanine 9.alpha.D-2'-deoxyriboside;6-thio-dG;beta-TGdR;9H-Purine-6-thiol, 2-amino-9-(2-deoxy-.alpha.-D-erythro-pentofuranosyl)-;9H-Purine-6(1H)-thione, 2-amino-9-(2-deoxy-.alpha.-D-erythro-pentofuranosyl)-;Guanosine, 2'-deoxy-6-thio-;NSC71261;NSC 71261;.beta.-TGdR;7-Deaza-dX;.alpha.-Deoxythioguanosine;NCIOpen2_003568;NCIOpen2_004523;thioguanine beta-deoxyriboside;.beta.-2'-Deoxythioguanosine;SCHEMBL536937;.beta.-2'-Deoxythiol guanosine;.beta.-Thioguanine deoxyriboside;CHEMBL1971770;SCHEMBL14156812;DTXSID50859540;6H-Purine-6-thione, 2-amino-9-(2-deoxy-.alpha.-D-erythro-pentofuranosyl)-1,9-dihydro-;9H-Purine-6(1H)-thione, 2-amino-9-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-;SCVJRXQHFJXZFZ-UHFFFAOYSA-N;.beta.-2'-Deoxy-6-thioguanosine;Thioguanine 9.beta.D-2'-deoxyriboside;NCI60_039359;NCI60_040806;FT-0665857;2-Amino-9-(2-deoxy-.alpha.-D-erythro-pentofuranosyl)mercaptopurine;2-Amino-9-(2-deoxypentofuranosyl)-3,9-dihydro-6H-purine-6-thione

Chemical Property of alpha-2'-Deoxythioguanosine

Chemical Property:

• Vapor Pressure: 4.22E-21mmHg at 25°C
• Melting Point: 190-192 °C
• Refractive Index: 1.93
• Boiling Point: 709.1°C at 760 mmHg
• PKA: 6.81±0.20(Predicted)
• Flash Point: 382.6°C
• PSA: 154.30000
• Density: 2.02g/cm³
• LogP: 0.29300
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), DMF (Slightly), Methanol (Slightly, Heated), Water (Very Slight
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 283.07391047
• Heavy Atom Count: 19
• Complexity: 420

Purity/Quality:

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

2''-Deoxy-6-thioGuanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Questionable carcinogen.
• Hazard Codes: Questionable carcinogen.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C2NC(=NC3=S)N)CO)O
• Uses: Guanosine (G837900) derivative with cancer chemotherapeutic properties. It is involved in the inhibition of human RNase H-mediated RNA cleavage from DNA-RNA duplexes via incorporation into DNA.

Technology Process of alpha-2'-Deoxythioguanosine

There total 8 articles about alpha-2'-Deoxythioguanosine 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: 100.0%

Isobutyric acid (2R,3S,5R)-5-(2-isobutyrylamino-6-thioxo-1,6-dihydro-purin-9-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester (136112-93-1) → 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine (789-61-7)

Guidance literature:

With sodium hydroxide; In ethanol;

DOI:10.1016/0040-4039(91)85095-M

Reference yield: 65.0%

2'-Deoxyguanosine (961-07-9) → 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine (789-61-7)

Guidance literature:

With sodium hydrogensulfide; trifluoroacetic anhydride; In pyridine; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19940770122

Reference yield:

2'-deoxy-N2-isobutyrylguanosine 3',5'-diisobutyrate (82921-42-4) → 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine (789-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1. triethylamine, dimethylaminopyridine, mesitylenesulphonyl chloride, 2a. N-methyl pyrrolidine, 2b. thiolacetic acid / 1. CH₂Cl₂, RT, 2a. ice bath, 2b. 30 min

2: 100 percent / 2 M NaOH / ethanol

With 1-Methylpyrrolidine; dmap; 2-mesitylenesulphonyl chloride; sodium hydroxide; triethylamine; tiolacetic acid; In ethanol;

DOI:10.1016/0040-4039(91)85095-M

upstream raw materials:

2'-Deoxyguanosine

Isobutyric acid (2R,3S,5R)-5-(2-isobutyrylamino-6-thioxo-1,6-dihydro-purin-9-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester

2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Downstream raw materials:

thioguanine

2-deoxy–α-D-ribose 1-phosphate

2'-deoxy-6-methylthioguanosine

2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine

Refernces

• 1、 Seela,Chen,Bindig,Kazimierczuk. "Synthesis of 2'-deoxyisoinosine and related 2'-deoxyribonucleosides". . p. 194 - 202. Retrieved 2007/10/02.
• 2、 Xu, Yao-Zhong,Zheng, Qinguo,Swann, Peter F.. "Simple synthesis of 4-thiothymidine, 4-thiouridine and 6-thio-2′-deoxyguanosine". . p. 2817 - 2820. Retrieved 2007/10/02.