(4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

Base Information

Chemical Name:(4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone
CAS No.:147753-89-7
Molecular Formula:C₂₃H₃₇NO₄Si
Molecular Weight:419.637
Hs Code.:

Synonyms:(4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

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Chemical Property of (4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

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Technology Process of (4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

There total 2 articles about (4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone 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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 147753-93-3
(4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

: 147753-89-7
(4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: With 1H-imidazole; In dichloromethane; Ambient temperature;
DOI:10.1021/jo00062a048

Reference yield:

: (4S,5R)-3-((R)-2,4-dimethylpent-4-enoyl)-4-methyl-5-phenyloxazolidin-2-one

: 147753-89-7
(4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 1) thexylborane, 2) NaHCO₃, 30percent aq. H₂O₂ / 1) THF, 36 h, -15 deg C, 2) MeOH, water, 1 h, 0 deg C

2: 98 percent / imidazole / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; thexylborane; dihydrogen peroxide; sodium hydrogencarbonate; In dichloromethane;
DOI:10.1021/jo00062a048

Reference yield:

: 147753-89-7
(4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

: 206123-70-8,648434-47-3
(3S,5R,6S)-3,5-dimethyl-6-isopropyl-3,4,5,6-tetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

2: Et₃N, pyridine*SO₃ / dimethylsulfoxide / 30 h / 25 °C

3: tetrahydrofuran / 1 h / Ambient temperature

4: Bu₄NF / tetrahydrofuran / 0.67 h / Heating

5: 100 percent / N-methylmorpholine N-oxide / RuCl₂(Ph₃P)3 / acetone / 5 h / Ambient temperature

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; 4-methylmorpholine N-oxide; triethylamine; tris(triphenylphosphine)ruthenium(II) chloride; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; acetone;
DOI:10.1021/jo00062a048