2-Chloro-2'-deoxy-3,7-dideazaadenosine

Base Information

• Chemical Name: 2-Chloro-2'-deoxy-3,7-dideazaadenosine
• CAS No.: 114915-05-8
• Molecular Formula: C₁₂H₁₄ClN₃O₃
• Molecular Weight: 283.714
• DSSTox Substance ID: DTXSID20150899
• Wikidata: Q83017205
• Mol file: 114915-05-8.mol

Synonyms:2-CDDDA;2-chloro-2'-deoxy-3,7-dideazaadenosine

Chemical Property of 2-Chloro-2'-deoxy-3,7-dideazaadenosine

Chemical Property:

• Melting Point: 209-212 °C
• Boiling Point: 624.7±55.0 °C(Predicted)
• PKA: 13.39±0.60(Predicted)
• Flash Point: 331.6oC
• PSA: 93.53000
• Density: 1.74±0.1 g/cm3(Predicted)
• LogP: 1.49380
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 283.0723690
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC3=C(N=C(C=C32)Cl)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@@H]1N2C=CC3=C(N=C(C=C32)Cl)N)CO)O

Technology Process of 2-Chloro-2'-deoxy-3,7-dideazaadenosine

There total 4 articles about 2-Chloro-2'-deoxy-3,7-dideazaadenosine 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:

4,6-Dichloro-1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl>-1H-pyrrolo<3,2-c>pyridine (91713-48-3) → 4-Amino-6-chloro-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrrolo<3,2-c>pyridine (114915-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NH₃ / methanol / 24 h / Ambient temperature

2: 1) N₂H₄*H₂O, 2) Raney nickel / 1) reflux, 1.5 h, 2) water, reflux, 45 min

With ammonia; nickel; hydrazine hydrate; In methanol;

DOI:10.1021/jm00127a011

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → 4-Amino-6-chloro-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrrolo<3,2-c>pyridine (114915-05-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / KOH, cryptand TDA-1 / acetonitrile / 0.75 h / Ambient temperature

2: 72 percent / NH₃ / methanol / 12 h / 50 °C

3: N₂H₄ / 1 h / 80 °C

4: Raney nickel / ethanol / 2 h / Heating

With potassium hydroxide; cryptand TDA-1; ammonia; nickel; hydrazine; In methanol; ethanol; acetonitrile;

DOI:10.1055/s-1988-27759

Reference yield:

4,6-Dichloro-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrrolo<3,2-c>pyridine (91713-49-4) → 4-Amino-6-chloro-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrrolo<3,2-c>pyridine (114915-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N₂H₄ / 1 h / 80 °C

2: Raney nickel / ethanol / 2 h / Heating

With nickel; hydrazine; In ethanol;

DOI:10.1055/s-1988-27759

upstream raw materials:

4,6-Dichloro-1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl>-1H-pyrrolo<3,2-c>pyridine

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

4,6-Dichloro-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrrolo<3,2-c>pyridine

4,6-dichloro-1H-pyrrolo<3,2-c>pyridine

Downstream raw materials:

4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolo<3,2-c>pyridine