Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester
• CAS No.: 153439-68-0
• Molecular Formula: C₁₇H₂₀N₄O₄
• Molecular Weight: 344.37

Synonyms:Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

Chemical Property of Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

There total 1 articles about Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[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: 88.0%

Benzoic acid (3aR,4R,6S,6aS)-6-cyano-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester → Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester (153439-68-0)

Guidance literature:

With lithium azide; pyridinium trifluroacetate; In pyridine; at 120 ℃;

DOI:10.1080/15257779908043088

Reference yield: 73.0%

dimethyl 3-chloro-2-pentenedioate (120461-65-6) + Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester (153439-68-0) → (Z)-3-[5-((3aS,4S,6R,6aR)-6-Benzoyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-tetrazol-2-yl]-pent-2-enedioic acid dimethyl ester (199184-03-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -5 ℃; for 4h;

DOI:10.1080/07328319708006198

Reference yield:

Benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(2H-tetrazol-5-yl)-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester (153439-68-0) → 3-((3aS,4S,6R,6aR)-6-Benzoyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-5-methoxycarbonylmethyl-1H-pyrazole-4-carboxylic acid methyl ester (199184-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / tetrahydrofuran / -5 °C

2: xylene / Thermolysis

With triethylamine; In tetrahydrofuran; xylene; 1: Addition / 2: Rearrangement;

DOI:10.1080/15257779908043088

Downstream raw materials:

(Z)-3-[5-((3aS,4S,6R,6aR)-6-Benzoyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-tetrazol-2-yl]-pent-2-enedioic acid dimethyl ester

3-((3aS,4S,6R,6aR)-6-Benzoyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-5-methoxycarbonylmethyl-1H-pyrazole-4-carboxylic acid methyl ester

3-[(1S,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)cyclopentyl]-1H-pyrazolo[4,3-c]pyridine-4,6(5H,7H)-dione

methyl {5-[(1S,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)cyclopentyl]-4-methoxycarbonyl-1H-pyrazolyl-3}acetate

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