(3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol

Base Information

• Chemical Name: (3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol
• CAS No.: 115511-73-4
• Molecular Formula: C₄₄H₅₂O₃Si
• Molecular Weight: 656.981

Synonyms:(3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol

Chemical Property of (3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol

There total 18 articles about (3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol (115511-73-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) CuBr*Me₂S / 1.) ether, hexane, 0 deg C, 6 min; 2.) -23 deg C, 20 min.

5: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

6: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

7: DMAP, pyridine / CH₂Cl₂ / 4 h / Ambient temperature

8: 71 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

9: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, hexane, 0 deg C, 20 min; 2.) THF, hexane, RT, 1 h 3.) THF, RT, 15 h

10: EDAC, DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

11: 85percent m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

12: CaCO₃, pyridine / toluene / 0.67 h / Heating

13: CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 20 min.

14: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

15: pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one (92512-33-9) → (3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol (115511-73-4)

Guidance literature:

Multi-step reaction with 17 steps

1: tetrahydrofuran / 0.25 h / Ambient temperature

2: Raney nickel / tetrahydrofuran / 4 h / Heating

3: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

4: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

5: 30percent H₂O₂ / 0 °C

6: 1.) CuBr*Me₂S / 1.) ether, hexane, 0 deg C, 6 min; 2.) -23 deg C, 20 min.

7: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

8: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

9: DMAP, pyridine / CH₂Cl₂ / 4 h / Ambient temperature

10: 71 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

11: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, hexane, 0 deg C, 20 min; 2.) THF, hexane, RT, 1 h 3.) THF, RT, 15 h

12: EDAC, DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

13: 85percent m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

14: CaCO₃, pyridine / toluene / 0.67 h / Heating

15: CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 20 min.

16: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

17: pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; nickel; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

D-Ribono-1,4-lactone (5336-08-3) → (3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-7-trityloxy-heptan-4-ol (115511-73-4)

Guidance literature:

Multi-step reaction with 18 steps

1: imidazole / dimethylformamide / 1 h / -20 - -15 °C

2: tetrahydrofuran / 0.25 h / Ambient temperature

3: Raney nickel / tetrahydrofuran / 4 h / Heating

4: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

5: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

6: 30percent H₂O₂ / 0 °C

7: 1.) CuBr*Me₂S / 1.) ether, hexane, 0 deg C, 6 min; 2.) -23 deg C, 20 min.

8: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

9: pyridine / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / Ambient temperature

10: DMAP, pyridine / CH₂Cl₂ / 4 h / Ambient temperature

11: 71 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

12: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, hexane, 0 deg C, 20 min; 2.) THF, hexane, RT, 1 h 3.) THF, RT, 15 h

13: EDAC, DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

14: 85percent m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

15: CaCO₃, pyridine / toluene / 0.67 h / Heating

16: CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 20 min.

17: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

18: pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; nickel; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)87683-3

upstream raw materials:

trityl chloride

(3S,4S,5S)-3,5-Dimethyl-7-trityloxy-heptane-1,4-diol

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

(3R,5R)-3,5-di-C-methyl-1-O-tert-butyldiphenylsilyl-7-O-triphenylmethyl-heptane 1,7-diol

Methanesulfonic acid (1R,2S)-1-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-2-methyl-4-trityloxy-butyl ester

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