7-(2-Deoxypentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Base Information

• Chemical Name: 7-(2-Deoxypentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• CAS No.: 60129-59-1
• Molecular Formula: C11H14N4O3
• Molecular Weight: 250.25
• DSSTox Substance ID: DTXSID70975559
• Mol file: 60129-59-1.mol

Synonyms:2'-deoxy-7-deazaadenosine;2'-deoxytubercidin;7-deaza-2'-deoxyadenosine

Chemical Property of 7-(2-Deoxypentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Chemical Property:

• Vapor Pressure: 2.62E-15mmHg at 25°C
• Refractive Index: 1.797
• Boiling Point: 601.3 °C at 760 mmHg
• Flash Point: 317.5 °C
• PSA: 106.42000
• Density: 1.75 g/cm³
• LogP: 0.23540
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 250.10659032
• Heavy Atom Count: 18
• Complexity: 306

Purity/Quality:

98%, ^*data from raw suppliers

Deoxytubercidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC3=C(N=CN=C32)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](OC1N2C=CC3=C(N=CN=C32)N)CO)O
• Uses: Deoxytubercidin was studied in mouse embryonic fibroblast and human colon cancer cell.

Technology Process of 7-(2-Deoxypentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

There total 27 articles about 7-(2-Deoxypentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-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: 95.0%

7-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-ribofuranosyl)-4-aminopyrrolo-[2,3-d]pyrimidine → 2'-deoxy-7-deazaadenosine (60129-59-1)

Guidance literature:

With ammonia; In methanol; at 0 - 20 ℃;

DOI:10.1002/chem.201102279

Reference yield: 90.0%

4-amino-2-chloro-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine (91741-81-0) → 2'-deoxy-7-deazaadenosine (60129-59-1)

Guidance literature:

With hydrogen; potassium carbonate; palladium on activated charcoal; In propan-1-ol; for 2h; under 1520 Torr;

DOI:10.1021/ja00333a046

Reference yield: 90.0%

6-chloro-2'-deoxytubercidin (97337-25-2) → 2'-deoxy-7-deazaadenosine (60129-59-1)

Guidance literature:

With hydrogen; potassium carbonate; palladium on activated charcoal; In propan-1-ol; water; for 8h; under 1520 Torr;

DOI:10.1021/jm00148a015

upstream raw materials:

4-amino-2-chloro-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

4-Amino-7-(2-desoxy-β-D-erythro-pentofuranosyl)-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin

4-chloro-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine

6-chloro-2'-deoxytubercidin

Downstream raw materials:

C₆₃H₆₇N₈O₁₂PSi

N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-P-methyl-2'-desoxytubercidylyl(3'->5')-N⁴-benzoyl-3'-O-(tert-butylmethylsilyl)-2'-desoxytubercidin

7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-7H-imidazo[1,2-c]-pyrrolo[2,3-d]pyrimidine

4-amino-7-(2-desoxy-β-D-erythro-pentofuranosyl)-5'-O-(4,4'-dimethoxytrityl)-7H-pyrrolo<2,3-d>pyrimidin

Refernces

• 1、 Maiti, Munmun,Michielssens, Servaas,Dyubankova, Natalia,Maiti, Mohitosh,Lescrinier, Eveline,Ceulemans, Arnout,Herdewijn, Piet. "Influence of the nucleobase and anchimeric assistance of the carboxyl acid groups in the hydrolysis of amino acid nucleoside phosphoramidates". supporting information; experimental part. p. 857 - 868. Retrieved 2012/03/26.
• 2、 Seela, Frank,Zulauf, Matthias. "Incorporation of 2'-deoxysangivamycin in DNA duplexes: The conversion of a pyrrolo[2,3-d]pyrimidine nitrile to a carboxamide upon oligonucleotide deprotection". . p. 2697 - 2709. Retrieved 2007/10/03.