tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

Chemical Name:tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:336625-41-3
Molecular Formula:C₃₃H₅₅NO₅
Molecular Weight:545.803
Hs Code.:

Synonyms:tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

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Chemical Property of tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

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Technology Process of tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

There total 7 articles about tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate 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: 91.0%

: 336625-40-2
tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-hydroxyhexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

: 336625-41-3
tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 4h;
DOI:10.1016/S0040-4020(00)01113-3

Reference yield:

: 122709-21-1,1822572-30-4
(4S)-2,2-Dimethyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidin-3-carbonsaeure-(tert-butyl)ester

: 336625-41-3
tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 76 percent / tetrahydrofuran; diethyl ether / 3 h / 0 °C

2: 70 percent / zinc borohydride / diethyl ether; benzene; tetrahydrofuran / 0.17 h / 20 °C

3: 97 percent / tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 20 °C

4: N-methylmorpholine N-oxide / OsO₄ / H₂O; acetone; toluene / 8 h / 20 °C

5: 1.53 g / NaIO₄ (on silica gel) / CH₂Cl₂ / 1 h / 0 °C

6: 76 percent / diethyl ether / 4 h / 20 °C

7: 91 percent / 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 4 h / 20 °C

With sodium periodate; zinc borohydride; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene; 6: Grignard reaction;
DOI:10.1016/S0040-4020(00)01113-3

Reference yield:

: 183603-94-3
tert-butyl (4S,1'R)-2,2-dimethyl-4-(1'-hydroxy-4'-pentenyl)oxazolidine-3-carboxylate

: 336625-41-3
tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxohexadecyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 20 °C

2: N-methylmorpholine N-oxide / OsO₄ / H₂O; acetone; toluene / 8 h / 20 °C

3: 1.53 g / NaIO₄ (on silica gel) / CH₂Cl₂ / 1 h / 0 °C

4: 76 percent / diethyl ether / 4 h / 20 °C

5: 91 percent / 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 4 h / 20 °C

With sodium periodate; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 4: Grignard reaction;
DOI:10.1016/S0040-4020(00)01113-3