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

Base Information

• Chemical Name: 4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester
• CAS No.: 88295-11-8
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396
• Mol file: 88295-11-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-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:

(-)-3a,8b-cis-dihydro-3H-5-carboxy-7-bromocyclopenta[b]benzofuran (88277-50-3) → 4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester (88295-11-8)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; hydrogenchloride; methanol; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; hydrogen; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; 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;

DOI:10.3987/com-00-8868

Reference yield:

4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester (88295-11-8) → beraprost (88475-69-8,88430-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; trifluoroacetic acid; dicyclohexyl-carbodiimide / benzene; dimethyl sulfoxide / 14 h / 20 °C

2.1: sodium hydroxide / 1,2-dimethoxyethane / 0.5 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate; methanol / 0.17 h / 10 °C

3.2: 7.5 h

4.1: sodium hydroxide / tetrahydrofuran / 30 - 35 °C

With pyridine; methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; dimethyl sulfoxide; benzene;

Reference yield:

4-((1S,2R,3aS,8bS)-2-Acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl)-butyric acid methyl ester (88295-11-8) → [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 (88430-50-6)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3.1: 134.2 g / CeCl₃*7H₂O; NaBH₄; satd. aq. NaHCO₃ / methanol / 1 h

4.1: NaOMe / methanol / 20 h / 20 °C

5.1: MnO₂ / CH₂Cl₂

5.2: CeCl₃*7H₂O; NaBH₄ / methanol

6.1: 47.6 percent / aq. NaOH / methanol / 28 h / 20 °C

With manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; sodium methylate; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; pyridine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: methanolysis / 5.1: Oxidation / 5.2: Reduction / 6.1: Hydrolysis;

DOI:10.3987/com-00-8868

upstream raw materials:

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

Downstream raw materials:

[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

beraprost

Refernces

• 1、 Nagase, Hiroshi,Matsumoto, Kazuhisa,Yoshiwara, Hideo,Tajima, Atsuko,Ohno, Kiyotaka. "Synthesis of (+)-5,6,7-trinor-4,8-inter-m-phenylene PGI2". . p. 4493 - 4494. Retrieved 2007/10/02.