methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate

Base Information

• Chemical Name: methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate
• CAS No.: 88277-19-4
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 88277-19-4.mol

Synonyms:

Chemical Property of methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate

There total 1 articles about methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate 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) → methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate (88277-19-4,132203-90-8)

Guidance literature:

Multi-step reaction with 11 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

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

DOI:10.3987/com-00-8868

Reference yield: 93.0%

methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate (88277-19-4,132203-90-8) + tert-butylchlorodiphenylsilane (58479-61-1) → C33H40O5Si

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 4h;

Reference yield:

methyl 4-((1S,2R,3aS,8bS)-2-hydroxy-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-5-yl)butanoate (88277-19-4,132203-90-8) → beraprost (88475-69-8,88430-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / N,N-dimethyl acetamide; dichloromethane / 5 h / 30 - 35 °C

2.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 5 °C

2.2: 6 h / 25 - 35 °C

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

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

With methanol; sodium tetrahydroborate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; sodium hydride; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide;

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.