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

Base Information

Chemical Name:tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-hydroxyhexadecyl)-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:336625-40-2
Molecular Formula:C₃₃H₅₇NO₅
Molecular Weight:547.819
Hs Code.:

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

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

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

There total 5 articles about tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-hydroxyhexadecyl)-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: 76.0%

: 15890-72-9
laurylmagnesium bromide

: 149180-94-9
tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxobutyl)-2,2-dimethyloxazolidine-3-carboxylate

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

Guidance literature:: In diethyl ether; 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

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

Guidance literature:: Multi-step reaction with 6 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

With sodium periodate; zinc borohydride; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; 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

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

Guidance literature:: Multi-step reaction with 4 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

With sodium periodate; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 4: Grignard reaction;
DOI:10.1016/S0040-4020(00)01113-3