6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine

Base Information

Chemical Name:6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine
CAS No.:259746-17-3
Molecular Formula:C₂₀H₁₉ClN₄O₅
Molecular Weight:430.848
Hs Code.:

Synonyms:6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine

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Chemical Property of 6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine

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Technology Process of 6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine

There total 4 articles about 6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-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: 64.0%

: 87-42-3
6-chloropurine

: 259746-16-2
1,2-di-O-acetyl-3,6-anhydro-5-O-benzyl-α,β-D-glucofuranose

: 259746-17-3
6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine

Guidance literature:: With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 70 - 80 ℃; for 0.666667h;
DOI:10.1016/S0040-4020(99)00911-4

Reference yield:

: 87-42-3
6-chloropurine

: 259746-16-2
1,2-di-O-acetyl-3,6-anhydro-5-O-benzyl-α,β-D-glucofuranose

: 259746-17-3
6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine

: Acetic acid (2R,3R,3aS,6R,6aR)-6-benzyloxy-2-(6-chloro-purin-7-yl)-hexahydro-furo[3,2-b]furan-3-yl ester

Guidance literature:: With benzenesulfonamide; tin(IV) chloride; In 1,2-dichloro-ethane; at 70 - 80 ℃; for 0.666667h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(99)00911-4

Reference yield:

: 27821-03-0
3,6-Anhydro-1,2-O-isopropyliden-α-D-glucofuranose

: 259746-17-3
6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 84 percent / tetrahydrofuran / 5 h / 20 °C

2.1: 74 percent / aq. H₂SO₄ / acetic acid / 5 h / 20 °C

3.1: 64 percent / BSA / TMSOTf / 1,2-dichloro-ethane / 0.67 h / 70 - 80 °C

With benzenesulfonamide; sulfuric acid; sodium hydride; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; acetic acid; 1,2-dichloro-ethane; 1.1: Substitution / 1.2: Etherification / 2.1: Hydrolysis / 3.1: Substitution;
DOI:10.1016/S0040-4020(99)00911-4