allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate

Base Information

Chemical Name:allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate
CAS No.:177325-45-0
Molecular Formula:C₂₂H₂₄N₂O₇
Molecular Weight:428.442
Hs Code.:

Synonyms:allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate

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Chemical Property of allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate

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Technology Process of allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate

There total 6 articles about allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate 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: 65.0%

: 127132-85-8
(6R,7S)-3-Acetoxymethyl-8-oxo-7-(2-phenoxy-acetylamino)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 106-95-6
allyl bromide

: 177325-45-0
allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate

Guidance literature:: With 4-methyl-morpholine; In N,N-dimethyl-formamide; at 0 - 40 ℃; for 14h;
DOI:10.1021/jm00168a019

Reference yield:

: 127023-91-0
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-vinyl-1-carba-1-dethia-3-cephem-4-carboxylate

: 177325-45-0
allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / O₃ / CH₂Cl₂; methanol / 0.67 h / -78 °C

2: lithium tri(tert-butoxy)aluminum hydride / tetrahydrofuran / 1 h / -35 °C

3: pyridine / tetrahydrofuran / 18 h / 0 °C

4: 70 percent / HOAc, zinc / CH₂Cl₂ / 2 h / 23 °C

5: 65 percent / N-methylmorpholine / dimethylformamide / 14 h / 0 - 40 °C

With 4-methyl-morpholine; pyridine; ozone; acetic acid; lithium tri-t-butoxyaluminum hydride; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00168a019

Reference yield:

: (6R,7S)-3-Hydroxymethyl-8-oxo-7-(2-phenoxy-acetylamino)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: 177325-45-0
allyl (7S,6R)-7-(phenoxyacetamido)-3-(acetoxymethyl)-1-carba-1-dethia-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / tetrahydrofuran / 18 h / 0 °C

2: 70 percent / HOAc, zinc / CH₂Cl₂ / 2 h / 23 °C

3: 65 percent / N-methylmorpholine / dimethylformamide / 14 h / 0 - 40 °C

With 4-methyl-morpholine; pyridine; acetic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00168a019