[(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl ester

Base Information

• Chemical Name: [(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl ester
• CAS No.: 90497-51-1
• Molecular Formula: C₂₈H₃₉NO₉P₂Si
• Molecular Weight: 623.652

Synonyms:

Chemical Property of [(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl ester

There total 4 articles about [(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl 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:

{(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,7-dioxo-1-aza-bicyclo[3.2.0]hept-2-yl}-phosphonic acid dimethyl ester (86509-46-8,90581-06-9) + chlorophosphoric acid diphenyl ester (2524-64-3) → [(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl ester (90497-51-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at -15 ℃;

DOI:10.1016/S0040-4039(00)99947-7

Reference yield:

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(methoxycarbonyl)methyl>azetidin-2-one (185446-92-8) → [(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl ester (90497-51-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) nBuLi / 1) THF, -78 deg C

2: 66 percent / 1,8-diazabicyclo(5.4.0)undec-7-ene, p-dodecylbenzenesulfonylazide / CH₂Cl₂

3: 74 percent / Rh₂(OAc)4 / CH₂Cl₂ / Heating

4: DBU / acetonitrile / -15 °C

With dirhodium tetraacetate; n-butyllithium; 4-dodecylbenzenesulphonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)99947-7

Reference yield:

(3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-propyl)-phosphonic acid dimethyl ester (86509-37-7,90581-02-5) → [(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-phosphonic acid dimethyl ester (90497-51-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / 1,8-diazabicyclo(5.4.0)undec-7-ene, p-dodecylbenzenesulfonylazide / CH₂Cl₂

2: 74 percent / Rh₂(OAc)4 / CH₂Cl₂ / Heating

3: DBU / acetonitrile / -15 °C

With dirhodium tetraacetate; 4-dodecylbenzenesulphonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)99947-7

upstream raw materials:

{(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,7-dioxo-1-aza-bicyclo[3.2.0]hept-2-yl}-phosphonic acid dimethyl ester

chlorophosphoric acid diphenyl ester

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(methoxycarbonyl)methyl>azetidin-2-one

(3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-propyl)-phosphonic acid dimethyl ester

Downstream raw materials:

{(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-2-yl}-phosphonic acid dimethyl ester

C₁₉H₂₃N₃O₉PS^(1-)*Na⁽¹⁺⁾

C₁₅H₁₇NO₅PS^(1-)*Na⁽¹⁺⁾

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