2-Chloro-9-pentopyranosyl-9h-purin-6-amine

Base Information

• Chemical Name: 2-Chloro-9-pentopyranosyl-9h-purin-6-amine
• CAS No.: 16755-02-5
• Molecular Formula: C₁₀H₁₂ClN₅O₄
• Molecular Weight: 301.689
• NSC Number: 101087
• DSSTox Substance ID: DTXSID20937349
• ChEMBL ID: CHEMBL1875220

Synonyms:MLS002703589;16755-02-5;2-chloro-9-pentopyranosyl-9h-purin-6-amine;NSC101087;CHEMBL1875220;DTXSID20937349;NSC-101087;SMR001570306

Chemical Property of 2-Chloro-9-pentopyranosyl-9h-purin-6-amine

Chemical Property:

• Vapor Pressure: 1.93E-13mmHg at 25°C
• Boiling Point: 561.4°C at 760 mmHg
• Flash Point: 293.3°C
• Density: 2.19g/cm³
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 301.0577816
• Heavy Atom Count: 20
• Complexity: 367

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)N)O)O)O

Technology Process of 2-Chloro-9-pentopyranosyl-9h-purin-6-amine

There total 4 articles about 2-Chloro-9-pentopyranosyl-9h-purin-6-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: 82.6%

2,6-dichloro-9-(2',3',4'-tri-O-benzoyl-β-D-ribopyranosyl)purine (672955-46-3) → 6-amino-2-chloro-9-(β-D-ribopyranosyl)purine (16755-02-5)

Guidance literature:

With ammonia; In methanol; at 100 ℃; for 7h;

DOI:10.1002/hlca.200390349

Reference yield:

2,6 dichloropurine (5451-40-1) → 6-amino-2-chloro-9-(β-D-ribopyranosyl)purine (16755-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90.3 percent / bis(trimethylsilyl)acetamide; TMS-OTf / acetonitrile / 3 h / 70 °C

2: 82.6 percent / NH₃ / methanol / 7 h / 100 °C

With trimethylsilyl trifluoromethanesulfonate; ammonia; bis-(trimethylsilyl)acetamide; In methanol; acetonitrile;

DOI:10.1002/hlca.200390349

Reference yield:

1,2,3,4-tetra-O-benzoyl-D-ribopyranose → 6-amino-2-chloro-9-(β-D-ribopyranosyl)purine (16755-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90.3 percent / bis(trimethylsilyl)acetamide; TMS-OTf / acetonitrile / 3 h / 70 °C

2: 82.6 percent / NH₃ / methanol / 7 h / 100 °C

With trimethylsilyl trifluoromethanesulfonate; ammonia; bis-(trimethylsilyl)acetamide; In methanol; acetonitrile;

DOI:10.1002/hlca.200390349

upstream raw materials:

2,6-dichloro-9-(2',3',4'-tri-O-benzoyl-β-D-ribopyranosyl)purine

2,6 dichloropurine

Downstream raw materials:

Benzoic acid (2R,3R,4R,5R)-2-(2-allyloxy-6-dibenzoylamino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-4-hydroxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3R,4S,5R)-2-(2-allyloxy-6-benzoylamino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-3-hydroxy-tetrahydro-pyran-4-yl ester

6-amino-N⁶,N⁶-dibenzoyl-9-{2'-O-benzoyl-3',4'-exo-O-[(4-methoxyphenyl)methylidene]-2-[(prop-2-enyl)oxy]-β-D-ribopyranosyl}purine

6-amino-N⁶,N⁶-dibenzoyl-9-(2'-O-benzoyl-β-D-ribopyranosyl)-2-[(prop-2-enyl)oxy]purine

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