(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-<<(methylsulfonyl)oxy>methyl>phenyl>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'-<<(methylsulfonyl)oxy>methyl>phenyl>carbonyl>ethyl>azetidin-2-one
CAS No.:107515-08-2
Molecular Formula:C₄₅H₅₄NO₈PSSi
Molecular Weight:828.051
Hs Code.:

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

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

There total 10 articles about (3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-<<(methylsulfonyl)oxy>methyl>phenyl>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: 96.0%

: 124-63-0
methanesulfonyl chloride

: 107515-06-0
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(hydroxymethyl)phenyl>carbonyl>ethyl>azetidin-2-one

: 107515-08-2
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-<<(methylsulfonyl)oxy>methyl>phenyl>carbonyl>ethyl>azetidin-2-one

Guidance literature:: With triethylamine; In dichloromethane; 1.) 0 deg C, 0.5 h, 2.) RT, 2 h;
DOI:10.1021/jm00388a022

Reference yield:

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

: 107515-08-2
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-<<(methylsulfonyl)oxy>methyl>phenyl>carbonyl>ethyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 8 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: 68 percent / tetrahydrofuran / 1 h / 0 °C

7: 79 percent / glacial acetic acid, tetra n-butylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature

8: 96 percent / triethylamine / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

With pyridine; thionyl chloride; 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

: 107515-08-2
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-<<(methylsulfonyl)oxy>methyl>phenyl>carbonyl>ethyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 8 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: 68 percent / tetrahydrofuran / 1 h / 0 °C

7: 79 percent / glacial acetic acid, tetra n-butylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature

8: 96 percent / triethylamine / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

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