(2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone

Base Information

• Chemical Name: (2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone
• CAS No.: 116511-43-4
• Molecular Formula: C₃₄H₄₂O₅SSi
• Molecular Weight: 590.856

Synonyms:

Chemical Property of (2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone

There total 12 articles about (2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone 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-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene (127785-50-6) → (2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone (116511-43-4)

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / DMAP / CH₂Cl₂ / 2 h / 0 °C

2: 81 percent / pyridinium tosylate / 3 h / Ambient temperature

3: 70 percent / N-methylmorpholine-N-oxide / OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 4 h / 0 °C

5: K₂CO₃ / 0.5 h / 0 °C

6: 1) (MeO)3CH, pyridinium tosylate, 2) Ac₂O / 1) room temp., 20 min, 2) 130 deg C, 45 min

7: 1) BH₃*Me₂S, 2) NaOH, H₂O₂ / 1) THF, -20 deg C, 5 h, 2) room temp., 30 min

8: 94 percent / PdCl₂(MeCN)2 / acetone / 2 h / Ambient temperature

9: diethyl ether; tetrahydrofuran / 2 h / -78 °C

10: Oxone / tetrahydrofuran; H₂O / 3 h / Ambient temperature

11: 1) (COCl)2, DMSO, 2) Et₃N / 1) -60 deg C, 20 min, 2) CH₂Cl₂, -60 deg C to room temp., 1 h

With dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; trimethyl orthoformate; dmap; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)96833-3

Reference yield:

5-<(tert-butyldiphenylsilyloxy)methyl>-4-methoxy-1-methyl-1,3-cyclohexadiene (116511-38-7) → (2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone (116511-43-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 81 percent / pyridinium tosylate / 3 h / Ambient temperature

2: 70 percent / N-methylmorpholine-N-oxide / OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

3: 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 4 h / 0 °C

4: K₂CO₃ / 0.5 h / 0 °C

5: 1) (MeO)3CH, pyridinium tosylate, 2) Ac₂O / 1) room temp., 20 min, 2) 130 deg C, 45 min

6: 1) BH₃*Me₂S, 2) NaOH, H₂O₂ / 1) THF, -20 deg C, 5 h, 2) room temp., 30 min

7: 94 percent / PdCl₂(MeCN)2 / acetone / 2 h / Ambient temperature

8: diethyl ether; tetrahydrofuran / 2 h / -78 °C

9: Oxone / tetrahydrofuran; H₂O / 3 h / Ambient temperature

10: 1) (COCl)2, DMSO, 2) Et₃N / 1) -60 deg C, 20 min, 2) CH₂Cl₂, -60 deg C to room temp., 1 h

With dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; trimethyl orthoformate; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)96833-3

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2S,4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohexanone (116511-43-4)

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / DMAP / CH₂Cl₂ / 2 h / 0 °C

2: 81 percent / pyridinium tosylate / 3 h / Ambient temperature

3: 70 percent / N-methylmorpholine-N-oxide / OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 4 h / 0 °C

5: K₂CO₃ / 0.5 h / 0 °C

6: 1) (MeO)3CH, pyridinium tosylate, 2) Ac₂O / 1) room temp., 20 min, 2) 130 deg C, 45 min

7: 1) BH₃*Me₂S, 2) NaOH, H₂O₂ / 1) THF, -20 deg C, 5 h, 2) room temp., 30 min

8: 94 percent / PdCl₂(MeCN)2 / acetone / 2 h / Ambient temperature

9: diethyl ether; tetrahydrofuran / 2 h / -78 °C

10: Oxone / tetrahydrofuran; H₂O / 3 h / Ambient temperature

11: 1) (COCl)2, DMSO, 2) Et₃N / 1) -60 deg C, 20 min, 2) CH₂Cl₂, -60 deg C to room temp., 1 h

With dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; trimethyl orthoformate; dmap; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)96833-3

upstream raw materials:

(+)-(1S,3S,4S,6S)-6-<(tert-butyldiphenylsilyloxy)methyl>-4-methyl-1-<1-methylene-3-(phenylsulphonyl)propyl>-1,3-cyclohexanediol

2-bromo-4-phenylthiobut-1-ene

(-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone

2-lithio-4-phenylthiobut-1-ene

Downstream raw materials:

(1S,2S,5S)-1-(3-Benzenesulfonyl-1-methylene-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-methyl-cyclohex-3-enol

(4S,5S)-5-(3-Benzenesulfonyl-1-methylene-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2-methyl-cyclohex-2-enone

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