(3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on

Base Information

• Chemical Name: (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on
• CAS No.: 154952-65-5
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317

Synonyms:(3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on

Chemical Property of (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on

Chemical Property:

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Technology Process of (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on

There total 5 articles about (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on 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: 91.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + (3aR,4S,6aS)-(+)-4-Hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on (154952-64-4) → (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on (154952-65-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 72h; Ambient temperature;

Reference yield:

(3aR,6aS)-(-)-6a-Methyl-3,3a,6,6a-tetrahydro-2H-cyclopentafuran-2-on (154635-32-2) → (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on (154952-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / 85percent m-chloroperbenzoic acid / CCl₄ / 0.33 h / Heating

2: 1.) Ph₂Se₂, NaBH₄; 2.) 30percent H₂O₂ / 1.) C₂H₅OH, 5 h, RT; 2.) THF; 1 h, 0 deg C; 1 h, RT; 4 h, reflux

3: 91 percent / pyridinium 4-toluenesulfonate / CH₂Cl₂ / 72 h / Ambient temperature

With sodium tetrahydroborate; diphenyl diselenide; dihydrogen peroxide; pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; In tetrachloromethane; dichloromethane;

Reference yield:

(3aS,5S,6aS)-5-Hydroxy-6a-methyl-hexahydro-cyclopenta[b]furan-2-one (154635-31-1) → (3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on (154952-65-5)

Guidance literature:

Multi-step reaction with 5 steps

1: NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 46 percent / pyridine / benzene / 0.75 h / 240 - 245 °C

3: 64 percent / 85percent m-chloroperbenzoic acid / CCl₄ / 0.33 h / Heating

4: 1.) Ph₂Se₂, NaBH₄; 2.) 30percent H₂O₂ / 1.) C₂H₅OH, 5 h, RT; 2.) THF; 1 h, 0 deg C; 1 h, RT; 4 h, reflux

5: 91 percent / pyridinium 4-toluenesulfonate / CH₂Cl₂ / 72 h / Ambient temperature

With pyridine; sodium tetrahydroborate; diphenyl diselenide; dihydrogen peroxide; pyridinium p-toluenesulfonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrachloromethane; dichloromethane; benzene;

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

(3aR,4S,6aS)-(+)-4-Hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-2-on

(3aR,6aS)-(-)-6a-Methyl-3,3a,6,6a-tetrahydro-2H-cyclopentafuran-2-on

(3aS,5S,6aS)-5-Hydroxy-6a-methyl-hexahydro-cyclopenta[b]furan-2-one

Downstream raw materials:

(1'S,4'S,5'S)-2-<4'-<3-(tert-Butyldimethylsilyloxy)-2,2-dimethylpropyl>-5'-(4-methoxybenzyloxy)-2'-methylcyclopent-2'-enyl>essigsaeure

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