Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester

Base Information

• Chemical Name: Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester
• CAS No.: 832078-96-3
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.271

Synonyms:Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester

Chemical Property of Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester

There total 1 articles about Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-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:

(R)-4-acetoxycyclopent-2-en-1-one (59995-48-1) → Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester (832078-96-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / K₂CO₃ / methanol

2: 86 percent / Et₃N; DMAP

3: 85 percent / toluene / 48 h / Heating

4: 80 percent / 18-crown-6; oxone; aq. NaHCO₃ / acetone; CH₂Cl₂ / 2 h / 0 °C

5: 81 percent / i-Pr₂NEt / CH₂Cl₂ / 48 h / 20 °C

6: 92 percent / pyridine

7: 73 percent / TBAF

8: 79 percent / CSA

With pyridine; dmap; Oxone; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetone; toluene; 4: Claisen-Eschenmoser rearrangement;

DOI:10.1055/s-2004-834822

Reference yield:

Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester (832078-96-3) → (R)-1-[(1S,2R,3R,5R)-2,3-bis(methoxymethoxy)-3-methyl-5-(triethylsilyloxy)cyclopentyl]-1-(4-methoxybenzyloxy)prop-2-en-2-yl trifluoromethanesulfonate

Guidance literature:

Multi-step reaction with 8 steps

1.1: 89 percent / K₂CO₃ / methanol

2.1: 86 percent / i-Pr₂NEt; NaI / CH₂Cl₂ / 18 h / Heating

3.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: 2-benzenesulfonyl-3-(3-nitrophenyl)oxaziridine / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.3: 74 percent / CSA / tetrahydrofuran; toluene / 1 h / -78 - 20 °C

4.1: 87 percent / CSA / CH₂Cl₂ / 18 h / 20 °C

5.1: 91 percent / toluene / 18 h / Heating

6.1: 88 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

7.1: 81 percent / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C

8.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

8.2: 91 percent / tetrahydrofuran; toluene / 1.17 h / -78 - 20 °C

With pyridine; camphor-10-sulfonic acid; potassium hexamethylsilazane; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1055/s-2004-834822

Reference yield:

Acetic acid (3aR,4R,5R,6aR)-5-methoxymethoxy-5-methyl-2-oxo-hexahydro-cyclopenta[b]furan-4-yl ester (832078-96-3) → (3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one (832078-90-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / K₂CO₃ / methanol

2.1: 86 percent / i-Pr₂NEt; NaI / CH₂Cl₂ / 18 h / Heating

3.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: 2-benzenesulfonyl-3-(3-nitrophenyl)oxaziridine / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.3: 74 percent / CSA / tetrahydrofuran; toluene / 1 h / -78 - 20 °C

4.1: 87 percent / CSA / CH₂Cl₂ / 18 h / 20 °C

With camphor-10-sulfonic acid; potassium hexamethylsilazane; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1055/s-2004-834822

upstream raw materials:

(R)-4-acetoxycyclopent-2-en-1-one

Downstream raw materials:

(3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

(R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

(1R)-1-[(1R,2R,3R,5R)-2,3-bis(methoxymethoxy)-3-methyl-5-[(triethylsilyl)oxy]cyclopentyl]-1-[(4-methoxyphenyl)methoxy]propan-2-one

(R)-2-[(1R,2R,3R,5R)-2,3-bis(methoxymethoxy)-3-methyl-5-(triethylsilyloxy)cyclopentyl]-2-(4-methoxybenzyloxy)-1-(pyrrolidin-1-yl)ethanone

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