(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

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Chemical Name:(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone
CAS No.:159622-45-4
Molecular Formula:C₂₅H₃₄N₂O₅Si
Molecular Weight:470.641
Hs Code.:

Synonyms:(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

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Chemical Property of (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

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Technology Process of (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

There total 12 articles about (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-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: 12.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: (S)-3-Amino-1-(tert-butyl-dimethyl-silanyl)-4-(4-methoxy-phenoxymethyl)-azetidin-2-one

: 159622-45-4
(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

: (3R,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

Guidance literature:: With sodium carbonate; In tetrahydrofuran; water; at 0 ℃; for 45h;
DOI:10.1016/S0040-4020(01)89309-1

Reference yield:

: 1877-75-4
2-(4-methoxyphenoxy)acetic acid

: 159622-45-4
(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 12 steps

1: pyridine, N,N'-carboxyldiimidazole, 4-dimethylaminopyridine / CH₂Cl₂ / 0 deg C, 1 h; room temp., 5 h

2: toluene / 0.75 h / 85 °C

3: 69 percent / ethanol; H₂O / 30 h / baker's yeast, immobilized on calcium alignate, fermented at 29 deg C, wit sucrose

4: hydrogen / 10percent Pd/C / ethanol / 2 h

5: N-ethyl-N'-(3-dimethylaminopropyl)carboidimide / H₂O; tetrahydrofuran / 1 h

6: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / Ambient temperature

7: hydrogen / 10percent Pd/C / methanol / 1 h

8: 30percent TiCl₃ / methanol; H₂O / 0.5 h / Ambient temperature; pH 7

9: 95 percent / Et₃N / dimethylformamide / 2 h / 20 °C / 1.) 0 deg C

10: 60 percent / lithium di-iso-propylamide, iso-amyl nitrite / tetrahydrofuran; hexane / 1 h / -78 °C

11: hydrogen / PtO₂ / ethyl acetate; H₂O / 12 h

12: 39 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 45 h / 0 °C

With pyridine; dmap; titanium(III) chloride; hydrogen; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; diethylazodicarboxylate; isopentyl nitrite; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)89309-1

Reference yield:

: 159622-40-9
(S) 4-<(4-methoxyphenoxy)methyl>-2-azetidinone

: 159622-45-4
(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / Et₃N / dimethylformamide / 2 h / 20 °C / 1.) 0 deg C

2: 60 percent / lithium di-iso-propylamide, iso-amyl nitrite / tetrahydrofuran; hexane / 1 h / -78 °C

3: hydrogen / PtO₂ / ethyl acetate; H₂O / 12 h

4: 39 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 45 h / 0 °C

With hydrogen; sodium carbonate; triethylamine; lithium diisopropyl amide; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; hexane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89309-1