(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate
• CAS No.: 165876-61-9
• Molecular Formula: C₂₇H₃₄O₅Si
• Molecular Weight: 466.649

Synonyms:(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

Chemical Property of (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

There total 2 articles about (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 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: 94.0%

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (165876-61-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1135/cccc19971325

Reference yield: 90.0%

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (58707-50-9,72777-85-6,81203-78-3,65025-94-7) + 4-biphenyl-carboxylic acid chloride (14002-51-8) → (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (165876-61-9)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bioorg.2016.09.003

Reference yield: 93.0%

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (165876-61-9) → (-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5)

Guidance literature:

With aluminium(III) chloride hexahydrate; In methanol; at 60 ℃; for 12h;

DOI:10.1016/j.bioorg.2016.09.003

upstream raw materials:

(-)-Corey lactone 5-(4-phenylbenzoate)

tert-butyldimethylsilyl chloride

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

4-biphenyl-carboxylic acid chloride

Downstream raw materials:

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

misoprostol

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