(4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

Base Information

Chemical Name:(4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one
CAS No.:371257-92-0
Molecular Formula:C₂₃H₃₇NO₆Si
Molecular Weight:451.635
Hs Code.:

Synonyms:(4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

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Chemical Property of (4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

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Technology Process of (4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

There total 7 articles about (4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-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: 94.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 371257-90-8
(4S,5R)-4-benzyloxymethyl-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

: 371257-92-0
(4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

Guidance literature:: With dmap; In chloroform; at 20 ℃; for 1h;
DOI:10.1021/jo015886j

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 371257-92-0
(4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / triflic acid / CH₂Cl₂; tetrahydrofuran / 48 h / 20 °C

2: 93 percent / NaBH₄ / tetrahydrofuran / 24 h / 20 °C

3: 82 percent / imidazole / dimethylformamide / 20 °C

4: 94 percent / DMAP / CHCl₃ / 1 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo015886j

Reference yield:

: 253350-02-6
(4R,5R)-4,5-di(isopropyloxycarbonyl)-3-benzoyloxazolidin-2-one

: 371257-92-0
(4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 89 percent / BF₃*OEt₂ / propan-2-ol / Heating

2.1: BF₃*OEt₂ / tetrahydrofuran / 4 h

2.2: 92 percent / NaBH₄ / tetrahydrofuran / 120 h / 20 °C

3.1: 90 percent / triflic acid / CH₂Cl₂; tetrahydrofuran / 48 h / 20 °C

4.1: 93 percent / NaBH₄ / tetrahydrofuran / 24 h / 20 °C

5.1: 82 percent / imidazole / dimethylformamide / 20 °C

6.1: 94 percent / DMAP / CHCl₃ / 1 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo015886j