[1,1'-Biphenyl]-4-carboxylic Acid (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl)hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl Ester

Base Information

• Chemical Name: [1,1'-Biphenyl]-4-carboxylic Acid (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl)hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl Ester
• CAS No.: 143399-99-9
• Molecular Formula: C₃₇H₃₈O₅Si
• Molecular Weight: 590.791
• Mol file: 143399-99-9.mol

Synonyms:(1SR,5RS,6SR,7RS)-(+/-)-7-<(4-biphenyl)carbonyloxy>-6-<(1,1-dimethylethyl)diphenylsilyloxy>methyl-2-oxabicyclo<3.3.0>octane-3-one

Chemical Property of [1,1'-Biphenyl]-4-carboxylic Acid (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl)hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl Ester

Chemical Property:

• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

[1,1''-Biphenyl]-4-carboxylicAcid(3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl)hexahydro-2-oxo-2H-cyclopenta[b]furan-5-ylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the preparation of prostaglandin derivatives

Technology Process of [1,1'-Biphenyl]-4-carboxylic Acid (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl)hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl Ester

There total 1 articles about [1,1'-Biphenyl]-4-carboxylic Acid (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl)hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl 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: 83.0%

<3aR(3aα,4α,5β,6aα)>-(-)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one (54382-73-9) + tert-butylchlorodiphenylsilane (58479-61-1) → (1SR,5RS,6SR,7RS)-(+/-)-7-<(4-biphenyl)carbonyloxy>-6-<(1,1-dimethylethyl)diphenylsilyloxy>methyl-2-oxabicyclo<3.3.0>octane-3-one (143399-99-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; 1) 0 deg C, 1 h, 2) RT, 18 h;

Reference yield: 87.0%

(1SR,5RS,6SR,7RS)-(+/-)-7-<(4-biphenyl)carbonyloxy>-6-<(1,1-dimethylethyl)diphenylsilyloxy>methyl-2-oxabicyclo<3.3.0>octane-3-one (143399-99-9) → (1SR,5RS,6SR,7RS)-(+/-)-6-<(1,1-dimethylethyl)diphenylsilyloxymethyl>-7-hydroxy-2-oxabicyclo<3.3.0>octane-3-one (87858-95-5)

Guidance literature:

With potassium carbonate; In methanol; dichloromethane; for 7h; Ambient temperature;

Reference yield:

(1SR,5RS,6SR,7RS)-(+/-)-7-<(4-biphenyl)carbonyloxy>-6-<(1,1-dimethylethyl)diphenylsilyloxy>methyl-2-oxabicyclo<3.3.0>octane-3-one (143399-99-9) → (1S,2R,3S,4R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(2-[1,3]dithian-2-ylidene-ethyl)-4-(tetrahydro-pyran-2-yloxy)-cyclopentanol (143400-00-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / K₂CO₃ / CH₂Cl₂; methanol / 7 h / Ambient temperature

2: 69 percent / p-TsOH*H₂O / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) RT, 1 h

3: diisobutylaluminium hydride / toluene / 1 h / -78 °C

4: 1) n-BuLi / 1) THF, hexane, -20 deg C to RT, 2) THF, 18 h, reflux

With n-butyllithium; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene;

upstream raw materials:

<3aR(3aα,4α,5β,6aα)>-(-)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one

tert-butylchlorodiphenylsilane

Downstream raw materials:

(1SR,5RS,6SR,7RS)-(+/-)-6-<(1,1-dimethylethyl)diphenylsilyloxymethyl>-7-hydroxy-2-oxabicyclo<3.3.0>octane-3-one

(1SR,5RS,6SR,7RS)-(+/-)-7'-<(1,1-dimethylethyl)diphenylsilyloxymethyl>-8'-(tetrahydro-2H-pyran-2-yloxy)spiro<1,3-dithian-2,3'-<2>oxabicyclo<4.3.0>nonane>

(1S,2R,3S,4R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(2-[1,3]dithian-2-ylidene-ethyl)-4-(tetrahydro-pyran-2-yloxy)-cyclopentanol

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