(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Base Information

• Chemical Name: (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• CAS No.: 107515-27-5
• Molecular Formula: C₃₀H₄₇NO₅Si₂
• Molecular Weight: 557.878
• Mol file: 107515-27-5.mol

Synonyms:(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Chemical Property of (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl 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-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

There total 9 articles about (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl 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: 69.0%

(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<<<4'-<(tert-butyldimethylsilyl)oxy>phenyl>carbonyl>methyl>azetidin-2-one (107515-03-7) → (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (107515-27-5)

Guidance literature:

With hydroquinone; In xylene; at 130 ℃; for 3.5h;

DOI:10.1021/jm00388a022

Reference yield:

diallyl tartarate (57833-54-2,61879-31-0,107596-43-0) → (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (107515-27-5)

Guidance literature:

Multi-step reaction with 7 steps

1: periodic acid / tetrahydrofuran / 1 h

2: 100 percent / toluene / 12 h / Heating

3: thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

4: 6.5 g / pyridine / dimethylformamide / 2 h / 80 °C

5: triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 51 percent / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

7: 69 percent / hydroquinone / xylene / 3.5 h / 130 °C

With pyridine; thionyl chloride; periodic acid; triethylamine; hydroquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; xylene;

DOI:10.1021/jm00388a022

Reference yield:

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one (88669-70-9) → (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (107515-27-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 66 percent / imidazole / dimethylformamide / 4 h / 47 °C

2: 100 percent / toluene / 12 h / Heating

3: thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

4: 6.5 g / pyridine / dimethylformamide / 2 h / 80 °C

5: triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 51 percent / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

7: 69 percent / hydroquinone / xylene / 3.5 h / 130 °C

With pyridine; 1H-imidazole; thionyl chloride; triethylamine; hydroquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; xylene;

DOI:10.1021/jm00388a022

upstream raw materials:

(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<<<4'-<(tert-butyldimethylsilyl)oxy>phenyl>carbonyl>methyl>azetidin-2-one

diallyl tartarate

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

allyl 2-oxoacetate

Downstream raw materials:

potassium (5R,6S)-2-(4'-hydroxyphenyl)-6-<(1R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate

allyl (5R,6S)-2-(4'-hydroxyphenyl)-6-<(1R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate