(3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

Base Information

Chemical Name:(3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone
CAS No.:90652-20-3
Molecular Formula:C₂₅H₂₇NO₆S
Molecular Weight:469.558
Hs Code.:

Synonyms:(3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

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Chemical Property of (3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

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Technology Process of (3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

There total 9 articles about (3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)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:

: 80675-54-3
((1-(phenylthio)vinyl)oxy)trimethylsilane

: 95342-50-0
(3S,4R)-4-acetoxy-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone

: 90652-20-3
(3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Ambient temperature;
DOI:10.1246/bcsj.58.3264

Reference yield:

: 98076-56-3
[(4-Methoxy-benzyl)-amino]-acetic Acid Tert-butyl Ester

: 90652-20-3
(3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

1: 71.5 percent / N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 20 - 30 °C

2: n-BuLi, hexamethyldisilazane / tetrahydrofuran; hexane / 1) 1) 2 to 3 deg C, 2) 20 to 23 deg C, 30 min

3: 5percent NaHCO₃ / ethyl acetate

4: trifluoroacetic acid / 3 h / 0 °C

5: 51.3 percent / dimethylformamide; acetic acid / 0.25 h / 50 - 55 °C

6: 4-dimethylaminopyridine

7: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Ambient temperature

With dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.58.3264

Reference yield:

: 95266-01-6
t-butyl (2S,3S)-3-<(R)-1-hydroxyethyl>-1-(4-methoxybenzyl)-4-oxo-2-azetidinecarboxylate

: 90652-20-3
(3S,4R)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid / 3 h / 0 °C

2: 51.3 percent / dimethylformamide; acetic acid / 0.25 h / 50 - 55 °C

3: 4-dimethylaminopyridine

4: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Ambient temperature

With dmap; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.58.3264