(4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one

Base Information

Chemical Name:(4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one
CAS No.:115479-81-7
Molecular Formula:C₂₈H₃₀O₃
Molecular Weight:414.544
Hs Code.:

Synonyms:(4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one

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Chemical Property of (4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one

Chemical Property:

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Technology Process of (4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one

There total 19 articles about (4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one 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:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 115479-81-7
(4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 13 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.

With pyridine; dmap; 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; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

: 115479-81-7
(4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 10 steps

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

2: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

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

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

5: 71 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

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

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

8: 85percent m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

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

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

With pyridine; dmap; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; dmap; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 103233-14-3
(4S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-methyldihydrofuran-2(3H)-one

: 115479-81-7
(4S,5R)-4-Methyl-5-((S)-1-methyl-3-trityloxy-propyl)-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / borane-dimethylsulphide complex / tetrahydrofuran / 15 h / Ambient temperature

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

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

4: 71 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

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

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

7: 85percent m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

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

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

With pyridine; dmap; n-butyllithium; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; dmap; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)87683-3