(3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione

Base Information

• Chemical Name: (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione
• CAS No.: 84786-91-4
• Molecular Formula: C₂₄H₂₈O₄Si
• Molecular Weight: 408.569

Synonyms:(3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione

Chemical Property of (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione

There total 7 articles about (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione 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: 99.0%

(1SR,5RS,6SR,7RS)-(+/-)-6-<(1,1-dimethylethyl)diphenylsilyloxymethyl>-7-hydroxy-2-oxabicyclo<3.3.0>octane-3-one (87858-95-5) → (3aS,4R,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione (84786-91-4,85994-88-3,87858-96-6)

Guidance literature:

With jones reagent; In acetone; at 5 ℃; for 0.75h;

DOI:10.1016/S0040-4039(00)88113-7

Reference yield:

cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aS,4R,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione (84786-91-4,85994-88-3,87858-96-6)

Guidance literature:

Multi-step reaction with 3 steps

2: 83 percent / imidazole / dimethylformamide / 1.5 h / 5 °C

3: 99 percent / Jones reagent / acetone / 0.75 h / 5 °C

With 1H-imidazole; jones reagent; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)88113-7

Reference yield:

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one (26054-65-9) → (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione (84786-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: K₂CO₃ / methanol / 1.5 h / 23 °C

3: 90 percent / diisopropylcarbodiimide, dichloroacetic acid / benzene; dimethylsulfoxide / 0.5 h / 23 °C

With dichloro-acetic acid; dmap; potassium carbonate; diisopropyl-carbodiimide; In methanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00344a047

upstream raw materials:

(3aS,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one

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

cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one

(+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one

Downstream raw materials:

Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester

C₄₁H₅₀O₆S₂Si

C₃₁H₃₈O₈S₂

C₃₁H₄₀O₈S₃

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