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

Base Information

• Chemical Name: (-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone
• CAS No.: 116511-47-8
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone 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: 98.0%

(-)-(7S,8S,10S)-10-<(tert-butyldiphenylsilyloxy)methyl>-8-methyl-1,4-dioxaspiro<4.5>decan-7-ol (116511-40-1) → (-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone (116511-47-8)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); In acetone; for 7h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

5-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene (127785-50-6) → (-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone (116511-47-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 18 h / 0 °C

2: 88 percent / pyridinium-p-toluenesulphonate / benzene / 16 h / Heating; Dean-Stark conditions

3: 71 percent / osmium tetroxide, N-methylmorpholine-N-oxide monohydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 43 percent / 1.) triethylamine; 2.) 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 0 °C / 1.) 10 min

5: 88 percent / potassium carbonate / methanol / 1 h / Ambient temperature

6: 100 percent / pyridinium-p-toluenesulphonate / CH₂Cl₂ / 0.33 h / Ambient temperature

7: 94 percent / acetic anhydride / 1 h / Heating

8: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 10 deg C, --> room temp., 16 h; 2.) H₂O, 0 deg C, 1 h

9: 98 percent / palladium(II) chloride-acetonitrile complex / acetone / 7 h / Ambient temperature

With dmap; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; osmium(VIII) oxide; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetic anhydride; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

5-<(tert-butyldiphenylsilyloxy)methyl>-4-methoxy-1-methyl-1,3-cyclohexadiene (116511-38-7) → (-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone (116511-47-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / pyridinium-p-toluenesulphonate / benzene / 16 h / Heating; Dean-Stark conditions

2: 71 percent / osmium tetroxide, N-methylmorpholine-N-oxide monohydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

3: 43 percent / 1.) triethylamine; 2.) 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 0 °C / 1.) 10 min

4: 88 percent / potassium carbonate / methanol / 1 h / Ambient temperature

5: 100 percent / pyridinium-p-toluenesulphonate / CH₂Cl₂ / 0.33 h / Ambient temperature

6: 94 percent / acetic anhydride / 1 h / Heating

7: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 10 deg C, --> room temp., 16 h; 2.) H₂O, 0 deg C, 1 h

8: 98 percent / palladium(II) chloride-acetonitrile complex / acetone / 7 h / Ambient temperature

With dmap; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; osmium(VIII) oxide; dimethylsulfide borane complex; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetic anhydride; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)89182-1

upstream raw materials:

(-)-(7S,8S,10S)-10-<(tert-butyldiphenylsilyloxy)methyl>-8-methyl-1,4-dioxaspiro<4.5>decan-7-ol

5-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene

5-<(tert-butyldiphenylsilyloxy)methyl>-4-methoxy-1-methyl-1,3-cyclohexadiene

(7R^*,8S^*10S^*)-10-<(tert-butyldiphenylsilyloxy)methyl>-8-methyl-1,4-dioxaspiro<4.5>decane-7,8-diol

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

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

(+)-5-desmethoxy-3,4S-dihydro-5-oxomilbemycin β₁ 7,8'-R-benzylidene acetal

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