(+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone

Base Information

Chemical Name:(+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone
CAS No.:614733-19-6
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:(+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone

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Chemical Property of (+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone

Chemical Property:

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Technology Process of (+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone

There total 6 articles about (+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone 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: 93.0%

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

: 614733-18-5
(+)-(3R,4S)-4-methyl-3-(benzyloxy)-2-azetidinone

: 614733-19-6
(+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone

Guidance literature:: With dmap; In acetonitrile; at 20 ℃; for 4h;
DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

: 160237-99-0
(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone

: 614733-19-6
(+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 20 °C

2: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

3: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

4: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

5: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

With dmap; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; triethylamine; sodium iodide; palladium on activated charcoal; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

: 160334-80-5
(-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone

: 614733-19-6
(+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

2: 100 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 20 °C

3: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

4: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

5: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

6: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

With dmap; sodium tetrahydroborate; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(03)01063-9