Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

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Chemical Name:Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester
CAS No.:147060-46-6
Molecular Formula:C₁₆H₁₄ClN₅O₄
Molecular Weight:375.771
Hs Code.:

Synonyms:Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

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Chemical Property of Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

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Technology Process of Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

There total 9 articles about Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester 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: 70.3%

: (-)-(2S,4R)-6-chloro-2-fluoro-9-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>purine

: Benzoic acid (2S,4R)-4-(6-amino-2-fluoro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

: 147060-46-6
Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

Guidance literature:: With ammonia; In 1,2-dimethoxyethane; for 15h; Ambient temperature;
DOI:10.1021/jm00057a001

Reference yield:

: 98-88-4
benzoyl chloride

: 147060-46-6
Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 83.4 percent / pyridine / CH₂Cl₂ / 2 h

2: 99.2 percent / p-TsOH / methanol / 3 h / Ambient temperature

3: NaIO₄, RuO₂ / H₂O; CCl₄; acetonitrile / 5 h

4: pyridine / tetrahydrofuran / 0.75 h

5: TMSOTf / CH₂Cl₂ / Ambient temperature

6: TMSOTf / CH₂Cl₂ / a) RT, overnight, b) 80 deg C, 1 h

7: 70.3 percent / NH₃ / 1,2-dimethoxy-ethane / 15 h / Ambient temperature

With pyridine; ruthenium(IV) oxide; sodium periodate; trimethylsilyl trifluoromethanesulfonate; ammonia; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile;
DOI:10.1021/jm00057a001

Reference yield:

: 1651-29-2
6-chloro-2-fluoropurine

: 147060-46-6
Benzoic acid (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: ammonium sulfate / 3 h / Heating

2: TMSOTf / CH₂Cl₂ / Ambient temperature

3: TMSOTf / CH₂Cl₂ / a) RT, overnight, b) 80 deg C, 1 h

4: 70.3 percent / NH₃ / 1,2-dimethoxy-ethane / 15 h / Ambient temperature

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; In 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jm00057a001