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

Base Information

• Chemical Name: (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(phenylcarbonyl)methyl>azetidin-2-one
• CAS No.: 107514-99-8
• Molecular Formula: C₄₂H₄₈NO₅PSi
• Molecular Weight: 705.906
• Mol file: 107514-99-8.mol

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

Chemical Property of (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(phenylcarbonyl)methyl>azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(phenylcarbonyl)methyl>azetidin-2-one

There total 8 articles about (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(phenylcarbonyl)methyl>azetidin-2-one 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: 52.0%

phenylmagnesium bromide + (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<<(2'-pyridylthio)carbonyl>methyl>azetidin-2-one (105248-57-5) → (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(phenylcarbonyl)methyl>azetidin-2-one (107514-99-8)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1021/jm00388a022

Reference yield:

diallyl tartarate (57833-54-2,61879-31-0,107596-43-0) → (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(phenylcarbonyl)methyl>azetidin-2-one (107514-99-8)

Guidance literature:

Multi-step reaction with 6 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: 52 percent / tetrahydrofuran / 0.25 h / 0 °C

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

DOI:10.1021/jm00388a022

Reference yield:

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one (88669-70-9) → (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(phenylcarbonyl)methyl>azetidin-2-one (107514-99-8)

Guidance literature:

Multi-step reaction with 6 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: 52 percent / tetrahydrofuran / 0.25 h / 0 °C

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

DOI:10.1021/jm00388a022

upstream raw materials:

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

allyl (5R,6S)-2-phenyl-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>carbapen-2-em-3-carboxylate

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

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