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

Base Information

Chemical Name:(3S,4R)-4-acetoxy-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone
CAS No.:95342-50-0
Molecular Formula:C₁₉H₂₃NO₇
Molecular Weight:377.394
Hs Code.:

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

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

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

There total 8 articles about (3S,4R)-4-acetoxy-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-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: 63.0%

: 546-67-8
lead(IV) tetraacetate

: 95266-09-4
(2S,3S)-3-<(R)-1-(allyloxycarbonyloxy)ethyl>-1-(4-methoxybenzyl)-4-oxo-2-azetidinecarboxylic acid

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

Guidance literature:: In acetic acid; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.58.3264

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With dmap; n-butyllithium; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; hexane; 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

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

Guidance literature:: Multi-step reaction with 3 steps

1: trifluoroacetic acid / 3 h / 0 °C

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

3: 4-dimethylaminopyridine

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