(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

Base Information

Chemical Name:(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester
CAS No.:127605-01-0
Molecular Formula:C₂₆H₄₂O₄SSi
Molecular Weight:478.769
Hs Code.:

Synonyms:(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

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Chemical Property of (E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

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Technology Process of (E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

There total 8 articles about (E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl 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:

: 5709-98-8
(R)-cyclohex-3-enecarboxylic acid

: 127605-01-0
(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) m-chloroperoxybenzoic acid, 2.) triethylamine / 1.) 0 degC, 4h, CCl₄; 2.) 55 degC, 3h

2: 100 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 21 h / Heating

3: 98 percent / sodium bicarbonate / 3 h / 23 °C

4: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 64 h / 23 °C

5: diisobutylaluminiumhydride / hexane / 0.5 h / -78 °C

6: 1.) Li; 2.) trifluoracetic acid / 1.) THF, -20 degC, 1.5 h; 2.) THF, 0 degC, 1 h

7: R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide, boron tribromide, diisopropylethylamine / 1.) CH₂Cl₂, -45 degC, 2.5 h; 2.) CH₂Cl₂, -78 degC, 2h

With R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide; dmap; 2,6-di-tert-butyl-4-methylpyridine; boron tribromide; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In hexane; dichloromethane;
DOI:10.1016/S0040-4039(01)93750-5

Reference yield:

: 116498-92-1
(1R,4R,5R)-4-hydroxy-6-oxabicyclo[3.2.1]octan-7-one

: 127605-01-0
(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 21 h / Heating

2: 98 percent / sodium bicarbonate / 3 h / 23 °C

3: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 64 h / 23 °C

4: diisobutylaluminiumhydride / hexane / 0.5 h / -78 °C

5: 1.) Li; 2.) trifluoracetic acid / 1.) THF, -20 degC, 1.5 h; 2.) THF, 0 degC, 1 h

6: R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide, boron tribromide, diisopropylethylamine / 1.) CH₂Cl₂, -45 degC, 2.5 h; 2.) CH₂Cl₂, -78 degC, 2h

With R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide; dmap; 2,6-di-tert-butyl-4-methylpyridine; boron tribromide; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In hexane; dichloromethane;
DOI:10.1016/S0040-4039(01)93750-5

Reference yield:

: 127604-95-9
(1R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.2.1]octan-7-one

: 127605-01-0
(E)-(2S,3S)-5-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-hydroxy-2,4-dimethyl-pent-4-enethioic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / sodium bicarbonate / 3 h / 23 °C

2: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 64 h / 23 °C

3: diisobutylaluminiumhydride / hexane / 0.5 h / -78 °C

4: 1.) Li; 2.) trifluoracetic acid / 1.) THF, -20 degC, 1.5 h; 2.) THF, 0 degC, 1 h

5: R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide, boron tribromide, diisopropylethylamine / 1.) CH₂Cl₂, -45 degC, 2.5 h; 2.) CH₂Cl₂, -78 degC, 2h

With R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide; 2,6-di-tert-butyl-4-methylpyridine; boron tribromide; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In hexane; dichloromethane;
DOI:10.1016/S0040-4039(01)93750-5