benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

Base Information

• Chemical Name: benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester
• CAS No.: 596103-09-2
• Molecular Formula: C₁₇H₂₀O₆S
• Molecular Weight: 352.408

Synonyms:benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

Chemical Property of benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

Chemical Property:

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Technology Process of benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

There total 13 articles about benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-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: 62.0%

acetic anhydride (108-24-7) + benzoic acid (3aS,4R,5R,6aR)-(3aS,4R,5S,6aR)-2,2-dimethyl-5-oxotetrahydro-5λ4-thieno[3,4-d][1,3]dioxol-4-yl methyl ester (683275-15-2) → benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-09-2)

Guidance literature:

at 100 ℃; for 6h;

DOI:10.1021/jm034098e

Reference yield: 54.0%

benzoic acid (3aS,4R,5R,6aR)-(3aS,4R,5S,6aR)-2,2-dimethyl-5-oxotetrahydro-5λ4-thieno[3,4-d][1,3]dioxol-4-yl methyl ester (683275-15-2) → benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-09-2)

Guidance literature:

With acetate source; at 100 ℃; for 8h;

Reference yield:

((3aS,4R,6aR)-2,2- dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol (596103-06-9) → benzoic acid (3aS,4R,6RS,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester (596103-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / pyridine / 6 h / 20 °C

2: 95 percent / m-CPBA / CH₂Cl₂ / 0.75 h / -78 °C

3: 62 percent / 6 h / 100 °C

With pyridine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 3: Pummerer reaction;

DOI:10.1021/jm050595e

upstream raw materials:

acetic anhydride

benzoic acid (3aS,4R,5R,6aR)-(3aS,4R,5S,6aR)-2,2-dimethyl-5-oxotetrahydro-5λ4-thieno[3,4-d][1,3]dioxol-4-yl methyl ester

2,3:5,6-di-O-isopropylidene-D-gulitol

D-gulono-1,4-lactone

Downstream raw materials:

benzoic acid (3aS,4R,6S,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

benzoic acid (3aS,4R,6R,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

Benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-cyclopropylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

Benzoic acid (3aS,4R,6R,6aR)-6-(2-chloro-6-cyclopentylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

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