(1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl ester
CAS No.:113218-46-5
Molecular Formula:C₁₄H₁₆O₅
Molecular Weight:264.278
Hs Code.:

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

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Chemical Property of (1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl ester

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Technology Process of (1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl ester

There total 1 articles about (1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl 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:

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

: 113218-46-5
(1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 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

With sodium hydroxide; sulfuric acid; hydrogen; acetic acid; palladium on activated charcoal; In methanol; 1: Prins reaction / 2: Hydrolysis / 3: Hydrogenolysis / 4: Etherification;
DOI:10.3987/com-00-8868

Reference yield:

: 113218-46-5
(1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl ester

: 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 8 steps

1: p-toluenesulfonic acid / tetrahydrofuran / 2 h

2: 329.8 g / LiAlH₄ / tetrahydrofuran / 1 h / -20 - -10 °C

3: 274.0 g / MnO₂ / CH₂Cl₂ / 15 h / 20 °C

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

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

6: 85.6 percent / concd. HCl / methanol / 1 h / 50 - 60 °C

7: 85.7 percent / H₂ / 10 percent Pd/C / methanol / 3 h

8: triethylamine / tetrahydrofuran / 5.5 h / Heating

With hydrogenchloride; manganese(IV) oxide; lithium aluminium tetrahydride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1: Etherification / 2: Reduction / 3: Oxidation / 4: Alkylation / 5: Methylation / 6: deetherification / 7: Hydrogenation / 8: Etherification;
DOI:10.3987/com-00-8868

Reference yield:

: 113218-46-5
(1S,2R,3aS,8bS)-2-Hydroxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-carboxylic acid methyl ester

: 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 9 steps

1: p-toluenesulfonic acid / tetrahydrofuran / 2 h

2: 329.8 g / LiAlH₄ / tetrahydrofuran / 1 h / -20 - -10 °C

3: 274.0 g / MnO₂ / CH₂Cl₂ / 15 h / 20 °C

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

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

6: 85.6 percent / concd. HCl / methanol / 1 h / 50 - 60 °C

7: 85.7 percent / H₂ / 10 percent Pd/C / methanol / 3 h

8: triethylamine / tetrahydrofuran / 5.5 h / Heating

9: pyridine / 6 h / Heating

With pyridine; hydrogenchloride; manganese(IV) oxide; lithium aluminium tetrahydride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1: Etherification / 2: Reduction / 3: Oxidation / 4: Alkylation / 5: Methylation / 6: deetherification / 7: Hydrogenation / 8: Etherification / 9: Acetylation;
DOI:10.3987/com-00-8868