4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester

Base Information

Chemical Name:4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester
CAS No.:848330-42-7
Molecular Formula:C₂₇H₄₀O₈
Molecular Weight:492.61
Hs Code.:

4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester

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Chemical Property of 4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester

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Technology Process of 4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester

There total 17 articles about 4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl 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:

: 121618-70-0,121618-62-0
(S)-2-(tert-butyldimethylsilanyloxymethyl)-2,6-dimethyl-hept-5-enal

: 848330-42-7
4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: 80 percent / NaH / 1,2-dimethoxy-ethane / 8 h / Heating

2.1: 94 percent / Et₃SiH / tris(triphenylphosphine)rhodium chloride / CH₂Cl₂ / 4 h / Heating

3.1: 93 percent / p-TsOH / benzene / 4 h / Heating

4.1: n-Bu₄NF / tetrahydrofuran / 8 h / Heating

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

6.1: 77 percent / CH₂Cl₂ / 8 h / -78 - 0 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

8.1: HCO₂NH₂ / Pd/C / methanol / 4 h / 20 °C

9.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

10.1: m-CPBA / CH₂Cl₂ / 4 h / 20 °C

11.1: 4-DMAP; DCC / CH₂Cl₂ / 24 h / Heating

12.1: LiBr; Et₃N / tetrahydrofuran / 2 h / Heating

13.1: 100 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C

14.1: (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine; KHMDS / tetrahydrofuran / 1 h / -78 °C

15.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

16.1: 90 percent / NaBH₄ / methanol / 0.08 h / 20 °C

17.1: diisobutylaluminium hydride / hexane; diethyl ether / 1 h / -78 °C

17.2: 70 percent / p-TsOH / 4 h / 20 °C

18.1: 4-DMAP; DCC / CH₂Cl₂ / 24 h / 20 °C

With triethylsilane; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; benzene; 1.1: Horner-Emmons reaction / 5.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 15.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2004.12.129

Reference yield:

: 848330-24-5
(R)-2,6-Dimethyl-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hept-5-enal

: 848330-42-7
4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 77 percent / CH₂Cl₂ / 8 h / -78 - 0 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

3.1: HCO₂NH₂ / Pd/C / methanol / 4 h / 20 °C

4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

5.1: m-CPBA / CH₂Cl₂ / 4 h / 20 °C

6.1: 4-DMAP; DCC / CH₂Cl₂ / 24 h / Heating

7.1: LiBr; Et₃N / tetrahydrofuran / 2 h / Heating

8.1: 100 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C

9.1: (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine; KHMDS / tetrahydrofuran / 1 h / -78 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

11.1: 90 percent / NaBH₄ / methanol / 0.08 h / 20 °C

12.1: diisobutylaluminium hydride / hexane; diethyl ether / 1 h / -78 °C

12.2: 70 percent / p-TsOH / 4 h / 20 °C

13.1: 4-DMAP; DCC / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium tetrahydroborate; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 2.1: Dess-Martin oxidation / 10.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2004.12.129

Reference yield:

: 848330-27-8
(R)-2,6-Dimethyl-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hept-5-en-1-ol

: 848330-42-7
4-Methoxymethoxy-benzoic acid (3R,3aS,4R,6aR)-6a-isopropyl-2-methoxy-4-methyl-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-hexahydro-cyclopenta[b]furan-3-yl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

2.1: 77 percent / CH₂Cl₂ / 8 h / -78 - 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

4.1: HCO₂NH₂ / Pd/C / methanol / 4 h / 20 °C

5.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

6.1: m-CPBA / CH₂Cl₂ / 4 h / 20 °C

7.1: 4-DMAP; DCC / CH₂Cl₂ / 24 h / Heating

8.1: LiBr; Et₃N / tetrahydrofuran / 2 h / Heating

9.1: 100 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C

10.1: (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine; KHMDS / tetrahydrofuran / 1 h / -78 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

12.1: 90 percent / NaBH₄ / methanol / 0.08 h / 20 °C

13.1: diisobutylaluminium hydride / hexane; diethyl ether / 1 h / -78 °C

13.2: 70 percent / p-TsOH / 4 h / 20 °C

14.1: 4-DMAP; DCC / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium tetrahydroborate; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 1.1: Dess-Martin oxidation / 3.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2004.12.129