6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine

Base Information

• Chemical Name: 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine
• CAS No.: 244140-86-1
• Molecular Formula: C₂₉H₂₅ClN₄O₃
• Molecular Weight: 512.995
• Mol file: 244140-86-1.mol

Synonyms:6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine

Chemical Property of 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine

There total 5 articles about 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine 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: 89.0%

trityl chloride (76-83-5) + 6-chloro-9-(3-deoxy-β-D-erythro-pentofuranosyl)-9H-purine (6982-08-7) → 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine (244140-86-1)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/S0040-4039(01)00136-8

Reference yield:

Inosine (58-63-9) → 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine (244140-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Et₃N; DMAP / dimethylformamide / 50 °C

With dmap; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-100002490

Reference yield:

9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-1,9-dihydro-6H-purine-6-one (125790-82-1) → 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine (244140-86-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / H₃PO₂; Et₃N; H₂NC(NH)C(Me)2-N=N-C(Me)2C(NH)NH₂*2HCl / acetonitrile; H₂O / pH 8.0

2: 99 percent / POCl₃; PhNMe₂; Et₄NCl / acetonitrile

3: 94 percent / NaOMe / methanol

4: 85 percent / 2,4,6-collidine / acetonitrile

With 2,4,6-trimethyl-pyridine; tetraethylammonium chloride; sodium methylate; hypophosphorous acid; α,α'-azodiizobutyramidine-dihydrochloride; N,N-dimethyl-aniline; triethylamine; trichlorophosphate; In methanol; water; acetonitrile;

DOI:10.1081/NCN-120021951

upstream raw materials:

trityl chloride

6-chloro-9-(3-deoxy-β-D-erythro-pentofuranosyl)-9H-purine

9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-1,9-dihydro-6H-purine-6-one

2',5'-di-O-acetyl-3'-deoxyinosine

Downstream raw materials:

6-chloro-9-[2,3-dideoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl]-9H-purine

6-chloro-9-[3-deoxy-2-O-(sulfurylimidazolyl)-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine

6-chloro-9-[3-deoxy-2-O-[(trifluoromethyl)sulfonyl]-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine

iodenosine