[(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester

Base Information

Chemical Name:[(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester
CAS No.:86509-49-1
Molecular Formula:C₂₃H₂₆NO₆P
Molecular Weight:443.436
Hs Code.:

Synonyms:[(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester

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Chemical Property of [(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester

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Technology Process of [(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester

There total 10 articles about [(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl 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: 40.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 86509-47-9
[(5S,6R)-6-((S)-1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]hept-2-yl]-phosphonic acid dibenzyl ester

: 86509-49-1
[(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester

Guidance literature:: In dichloromethane; at 25 ℃; for 48h;
DOI:10.1016/S0040-4039(00)81403-3

Reference yield:

: 19236-58-9
dibenzyl methylphosphonate

: 86509-49-1
[(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 64 percent / nBuLi / tetrahydrofuran / -78 - 25 °C

2: 95 percent / tetrabutylammonium fluoride / CH₂Cl₂ / -78 °C

3: 80 percent / HCl / methanol / 4 h / 0 °C

4: 75 percent / p-carboxybenzenesulfonylazide, triethylamine / acetonitrile / 15 h / 15 °C

5: Rh₂(OAc)4 / benzene / 0.17 h / 80 °C

6: 40 percent / CH₂Cl₂ / 48 h / 25 °C

With hydrogenchloride; dirhodium tetraacetate; n-butyllithium; p-carboxybenzenesulfonyl azide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)81403-3

Reference yield:

: 538-60-3
dibenzyl hydrogen phosphite

: 86509-49-1
[(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NaH / dimethylformamide / 0 °C

2: 64 percent / nBuLi / tetrahydrofuran / -78 - 25 °C

3: 95 percent / tetrabutylammonium fluoride / CH₂Cl₂ / -78 °C

4: 80 percent / HCl / methanol / 4 h / 0 °C

5: 75 percent / p-carboxybenzenesulfonylazide, triethylamine / acetonitrile / 15 h / 15 °C

6: Rh₂(OAc)4 / benzene / 0.17 h / 80 °C

7: 40 percent / CH₂Cl₂ / 48 h / 25 °C

With hydrogenchloride; dirhodium tetraacetate; n-butyllithium; p-carboxybenzenesulfonyl azide; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)81403-3