4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester

Base Information

Chemical Name:4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester
CAS No.:223556-67-0
Molecular Formula:C₂₅H₃₂O₅
Molecular Weight:412.526
Hs Code.:

4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester

Synonyms:4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester

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Chemical Property of 4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester

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Technology Process of 4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester

There total 1 articles about 4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric 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

: 223556-67-0
4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 18 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

7: 274.0 g / MnO₂ / CH₂Cl₂ / 15 h / 20 °C

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

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

10: 85.6 percent / concd. HCl / methanol / 1 h / 50 - 60 °C

11: 85.7 percent / H₂ / 10 percent Pd/C / methanol / 3 h

12: triethylamine / tetrahydrofuran / 5.5 h / Heating

13: pyridine / 6 h / Heating

14: aq. HCl; MeOH / 2 h / 30 °C

15: N,N'-dicyclohexylcarbodiimide; DMSO; trifluoroacetic acid / pyridine / tetrahydrofuran / 10 h / 20 °C

16: NaH / tetrahydrofuran / 3 h / 10 °C

17: 134.2 g / CeCl₃*7H₂O; NaBH₄; satd. aq. NaHCO₃ / methanol / 1 h

18: NaOMe / methanol / 20 h / 20 °C

With pyridine; hydrogenchloride; methanol; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; sulfuric acid; hydrogen; sodium methylate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; pyridine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1: Prins reaction / 2: Hydrolysis / 3: Hydrogenolysis / 4: Etherification / 5: Etherification / 6: Reduction / 7: Oxidation / 8: Alkylation / 9: Methylation / 10: deetherification / 11: Hydrogenation / 12: Etherification / 13: Acetylation / 14: acidolysis / 15: Oxidation / 16: Condensation / 17: Reduction / 18: methanolysis;
DOI:10.3987/com-00-8868

Reference yield:

: 223556-67-0
4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester

: 88430-50-6
[1R,2R,3aS, 8bS]-(2,3,3a,8b-tetrahydro-2-hydroxyl-1-[(3S,4S)-3-hydroxyl-4-methyl-1-(E)-octen-6-ynyl]-1H-cyclopenta[b]benzofuran-5)-butanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: MnO₂ / CH₂Cl₂

1.2: CeCl₃*7H₂O; NaBH₄ / methanol

2.1: 47.6 percent / aq. NaOH / methanol / 28 h / 20 °C

With manganese(IV) oxide; sodium hydroxide; In methanol; dichloromethane; 1.1: Oxidation / 1.2: Reduction / 2.1: Hydrolysis;
DOI:10.3987/com-00-8868