Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester
CAS No.:133105-13-2
Molecular Formula:C₂₀H₂₄O₆
Molecular Weight:360.407
Hs Code.:

Synonyms:Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

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Chemical Property of Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

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Technology Process of Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

There total 10 articles about Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-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: 76.0%

: 133076-83-2,133162-58-0
(3aS,4aR,7S,7aR,8aR)-7-Hydroxymethyl-2,2,3a-trimethyl-hexahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-one

: 98-88-4
benzoyl chloride

: 133105-13-2
Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

Guidance literature:: With pyridine;
DOI:10.1016/S0040-4039(00)98006-7

Reference yield:

: 7086-66-0
2-<(1RS)-4-methylcyclohex-3-enyl>acetic acid

: 133105-13-2
Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1) NIS KOtBu / 1) DMF 2) rotary evaporation, 50 deg C

2: 88 percent / Na₂CO₃

3: 96 percent / MCPBA / CH₂Cl₂ / 0 °C

4: 74 percent / TMSBr, Ph₃P / CHCl₃ / -30 °C

5: 87 percent / p-TsOH / acetone

6: 97 percent / KOtBu / dimethylformamide / Heating

7: 82 percent / KI, I₂, NaHCO₃, H₂O / 72 h / 25 °C

8: 95 percent / nBu₃SnH / tetrahydrofuran / Heating

9: 1) LDA / 1) THF, -78 deg C 2) -40 deg C

10: 76 percent / pyridine

With pyridine; N-iodo-succinimide; trimethylsilyl bromide; potassium tert-butylate; water; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(00)98006-7

Reference yield:

: 133076-77-4
(1R,5R)-8-Methyl-2-oxa-bicyclo[3.3.1]non-7-en-3-one

: 133105-13-2
Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / Na₂CO₃

2: 96 percent / MCPBA / CH₂Cl₂ / 0 °C

3: 74 percent / TMSBr, Ph₃P / CHCl₃ / -30 °C

4: 87 percent / p-TsOH / acetone

5: 97 percent / KOtBu / dimethylformamide / Heating

6: 82 percent / KI, I₂, NaHCO₃, H₂O / 72 h / 25 °C

7: 95 percent / nBu₃SnH / tetrahydrofuran / Heating

8: 1) LDA / 1) THF, -78 deg C 2) -40 deg C

9: 76 percent / pyridine

With pyridine; trimethylsilyl bromide; potassium tert-butylate; water; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(00)98006-7