(3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one

Base Information

• Chemical Name: (3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one
• CAS No.: 114066-25-0
• Molecular Formula: C₂₅H₄₀O₄SSi₂
• Molecular Weight: 492.827

Synonyms:(3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one

Chemical Property of (3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one

Chemical Property:

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Technology Process of (3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one

There total 1 articles about (3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one 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:

5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene (114179-39-4) + benzenesulfenyl chloride (931-59-9) → (3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one (114066-25-0)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)96345-7

Reference yield: 100.0%

(3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one (114066-25-0) → (3aR,4S,5S,7aR)-3a-Hydroxy-4-hydroxymethyl-6-methyl-5-phenylsulfanyl-3a,4,5,7a-tetrahydro-benzofuran-3-one (179815-52-2)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1021/ja961071u

Reference yield: 82.0%

(3aR,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-3-one (114066-25-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → [(3aS,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-(3E)-ylidene]-acetic acid ethyl ester (179815-56-6)

Guidance literature:

In toluene; at 110 ℃;

DOI:10.1021/ja961071u

upstream raw materials:

5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

benzenesulfenyl chloride

Downstream raw materials:

(3aR,4S,5S,7aR)-3a-Hydroxy-4-hydroxymethyl-6-methyl-5-phenylsulfanyl-3a,4,5,7a-tetrahydro-benzofuran-3-one

[(3aS,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-(3E)-ylidene]-acetic acid ethyl ester

2-[(3aS,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-(3E)-ylidene]-ethanol

[(3aS,4S,5S,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-5-phenylsulfanyl-3a-trimethylsilanyloxy-3a,4,5,7a-tetrahydro-benzofuran-(3E)-ylidene]-acetaldehyde

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