[(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol

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Chemical Name:[(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol
CAS No.:132490-10-9
Molecular Formula:C₂₃H₃₂O₆
Molecular Weight:404.503
Hs Code.:

Synonyms:[(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol

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Chemical Property of [(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol

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Technology Process of [(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol

There total 1 articles about [(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol 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:

: 88277-50-3
(-)-3a,8b-cis-dihydro-3H-5-carboxy-7-bromocyclopenta[b]benzofuran

: 132490-10-9
[(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: acetic acid; concd. sulfuric acid / 4.5 h / 80 °C

2: aq. NaOH / aq. methanol / 2 h / Heating

3: H₂ / 10 percent Pd/C / methanol

4: 12 h / Heating

5: p-toluenesulfonic acid / tetrahydrofuran / 2 h

6: 329.8 g / LiAlH₄ / tetrahydrofuran / 1 h / -20 - -10 °C

With sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; hydrogen; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Prins reaction / 2: Hydrolysis / 3: Hydrogenolysis / 4: Etherification / 5: Etherification / 6: Reduction;
DOI:10.3987/com-00-8868

Reference yield:

: 132490-10-9
[(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol

: 4-((1S,2R,3aS,8bS)-2-Hydroxy-1-trityloxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 274.0 g / MnO₂ / CH₂Cl₂ / 15 h / 20 °C

2: DMSO, sodium salt / tetrahydrofuran / 18 h / 10 - 50 °C

3: dimethylsulfoxide; tetrahydrofuran / 14 h / 20 °C

4: 85.6 percent / concd. HCl / methanol / 1 h / 50 - 60 °C

5: 85.7 percent / H₂ / 10 percent Pd/C / methanol / 3 h

6: triethylamine / tetrahydrofuran / 5.5 h / Heating

With hydrogenchloride; manganese(IV) oxide; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1: Oxidation / 2: Alkylation / 3: Methylation / 4: deetherification / 5: Hydrogenation / 6: Etherification;
DOI:10.3987/com-00-8868

Reference yield:

: 132490-10-9
[(1S,2R,3aS,8bS)-2-(Tetrahydro-pyran-2-yloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-methanol

: 4-((1S,2R,3aS,8bS)-2-Acetoxy-1-trityloxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 274.0 g / MnO₂ / CH₂Cl₂ / 15 h / 20 °C

2: DMSO, sodium salt / tetrahydrofuran / 18 h / 10 - 50 °C

3: dimethylsulfoxide; tetrahydrofuran / 14 h / 20 °C

4: 85.6 percent / concd. HCl / methanol / 1 h / 50 - 60 °C

5: 85.7 percent / H₂ / 10 percent Pd/C / methanol / 3 h

6: triethylamine / tetrahydrofuran / 5.5 h / Heating

7: pyridine / 6 h / Heating

With pyridine; hydrogenchloride; manganese(IV) oxide; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1: Oxidation / 2: Alkylation / 3: Methylation / 4: deetherification / 5: Hydrogenation / 6: Etherification / 7: Acetylation;
DOI:10.3987/com-00-8868