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

Base Information

• Chemical Name: (1S,2S,5S)-1-(3-Benzenesulfonyl-1-methylene-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-methyl-cyclohex-3-enol
• CAS No.: 116511-45-6
• Molecular Formula: C₃₅H₄₄O₅SSi
• Molecular Weight: 604.883

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (1S,2S,5S)-1-(3-Benzenesulfonyl-1-methylene-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-methyl-cyclohex-3-enol 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) → (1S,2S,5S)-1-(3-Benzenesulfonyl-1-methylene-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-methyl-cyclohex-3-enol (116511-45-6)

Guidance literature:

Multi-step reaction with 14 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

12: 1) PhSeCl, 2) m-CPBA, aq. NaHCO₃ / 1) EtOAc, room temp., 2 h, 2) 10 deg C, 15 min

13: NaBH(OAc)3 / acetic acid / 0.5 h / Ambient temperature

14: HBF₄ / 0.33 h / -78 - 20 °C

With dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; tetrafluoroboric acid; Phenylselenyl chloride; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetic anhydride; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate; dmap; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; 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) → (1S,2S,5S)-1-(3-Benzenesulfonyl-1-methylene-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-methyl-cyclohex-3-enol (116511-45-6)

Guidance literature:

Multi-step reaction with 13 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

11: 1) PhSeCl, 2) m-CPBA, aq. NaHCO₃ / 1) EtOAc, room temp., 2 h, 2) 10 deg C, 15 min

12: NaBH(OAc)3 / acetic acid / 0.5 h / Ambient temperature

13: HBF₄ / 0.33 h / -78 - 20 °C

With dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; tetrafluoroboric acid; Phenylselenyl chloride; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetic anhydride; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; acetone; tert-butyl alcohol;

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

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1S,2S,5S)-1-(3-Benzenesulfonyl-1-methylene-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-methyl-cyclohex-3-enol (116511-45-6)

Guidance literature:

Multi-step reaction with 14 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

12: 1) PhSeCl, 2) m-CPBA, aq. NaHCO₃ / 1) EtOAc, room temp., 2 h, 2) 10 deg C, 15 min

13: NaBH(OAc)3 / acetic acid / 0.5 h / Ambient temperature

14: HBF₄ / 0.33 h / -78 - 20 °C

With dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; tetrafluoroboric acid; Phenylselenyl chloride; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetic anhydride; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate; dmap; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; acetone; tert-butyl alcohol;

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

upstream raw materials:

diazomethane

2-bromo-4-phenylthiobut-1-ene

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

2-lithio-4-phenylthiobut-1-ene

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