(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

Base Information

Chemical Name:(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one
CAS No.:107515-11-7
Molecular Formula:C₄₃H₅₀N₅O₅PSi
Molecular Weight:775.96
Hs Code.:

(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

Synonyms:(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

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Chemical Property of (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

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Technology Process of (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

There total 11 articles about (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>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: 53.0%

: 107515-09-3
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<2'-<<(methylsulfonyl)oxy>methyl>-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

: 107515-11-7
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

Guidance literature:: With lithium azide; In N,N-dimethyl-formamide; for 2h; Ambient temperature;
DOI:10.1021/jm00388a022

Reference yield:

: 57833-54-2,61879-31-0,107596-43-0
diallyl tartarate

: 107515-11-7
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: periodic acid / tetrahydrofuran / 1 h

2: toluene / 12 h / Heating

3: 6.2 g / thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

4: 13.9 g / dimethylformamide / 1.5 h / Ambient temperature

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

6: 56 percent / tetrahydrofuran / 1 h / 0 °C

7: 80 percent / glacial acetic acid, tetra n-butylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature

8: 100 percent / triethylamine / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

9: 53 percent / LiN₃ / dimethylformamide / 2 h / Ambient temperature

With pyridine; thionyl chloride; lithium azide; tetrabutyl ammonium fluoride; acetic acid; periodic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00388a022

Reference yield:

: 93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2
(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

: 107515-11-7
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)-5'-pyridyl>carbonyl>ethyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 73 percent / imidazole / dimethylformamide / 4 h / 47 °C

2: toluene / 12 h / Heating

3: 6.2 g / thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

4: 13.9 g / dimethylformamide / 1.5 h / Ambient temperature

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

6: 56 percent / tetrahydrofuran / 1 h / 0 °C

7: 80 percent / glacial acetic acid, tetra n-butylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature

8: 100 percent / triethylamine / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

9: 53 percent / LiN₃ / dimethylformamide / 2 h / Ambient temperature

With pyridine; 1H-imidazole; thionyl chloride; lithium azide; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00388a022