(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one

Base Information

Chemical Name:(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one
CAS No.:336625-42-4
Molecular Formula:C₃₀H₅₁NO₅
Molecular Weight:505.739
Hs Code.:

Synonyms:(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one

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Chemical Property of (2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one

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Technology Process of (2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one

There total 8 articles about (2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-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: 83.0%

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

: 336625-42-4
(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one

Guidance literature:: With acetic acid; at 20 ℃; for 12h;
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

: 336625-42-4
(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one

Guidance literature:: Multi-step reaction with 8 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

8: 83 percent / aqueous acetic acid / 12 h / 20 °C

With sodium periodate; zinc borohydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 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:

: 183603-95-4
tert-butyl (4S)-2,2-dimethyl-4-(1'-oxo-4'-pentenyl)oxazolidine-3-carboxylate

: 336625-42-4
(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)-1-hydroxyoctadecane-6-one

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / zinc borohydride / diethyl ether; benzene; tetrahydrofuran / 0.17 h / 20 °C

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

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

4: 1.53 g / NaIO₄ (on silica gel) / CH₂Cl₂ / 1 h / 0 °C

5: 76 percent / diethyl ether / 4 h / 20 °C

6: 91 percent / 2-iodoxybenzoic acid / dimethylsulfoxide; tetrahydrofuran / 4 h / 20 °C

7: 83 percent / aqueous acetic acid / 12 h / 20 °C

With sodium periodate; zinc borohydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 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; 5: Grignard reaction;
DOI:10.1016/S0040-4020(00)01113-3