(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

Base Information

Chemical Name:(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester
CAS No.:176220-76-1
Molecular Formula:C₂₄H₂₅NO₅S
Molecular Weight:439.532
Hs Code.:

Synonyms:(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

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Chemical Property of (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

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Technology Process of (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

There total 7 articles about (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 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: 75.0%

: 305796-41-2
(2S,5R,6R)-6-bromo-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

: 176220-76-1
(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 20 ℃; for 3h;
DOI:10.1021/ol006256r

Reference yield:

: 81324-43-8
(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

: 176220-76-1
(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / AIBN / toluene / 6 h / Heating

2: 75 percent / tributyltin hydride; AIBN / toluene / 3 h / 20 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; 1: Substitution / 2: Substitution;
DOI:10.1021/ol006256r

Reference yield:

: 24158-88-1
6,6-dibromopenicillanic acid

: 176220-76-1
(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 56 percent / potassium permanganate; phosphoric acid / H₂O

2: 95 percent / acetone / 2 h / 20 °C

3: 72 percent / AIBN / toluene / 6 h / Heating

4: 75 percent / tributyltin hydride; AIBN / toluene / 3 h / 20 °C

With potassium permanganate; 2,2'-azobis(isobutyronitrile); phosphoric acid; tri-n-butyl-tin hydride; In water; acetone; toluene; 1: Oxidation / 2: Alkylation / 3: Substitution / 4: Substitution;
DOI:10.1021/ol006256r