allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

Base Information

Chemical Name:allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate
CAS No.:107515-16-2
Molecular Formula:C₂₆H₃₆N₄O₄Si
Molecular Weight:496.682
Hs Code.:

Synonyms:allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

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Chemical Property of allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

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Technology Process of allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

There total 12 articles about allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate 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: 71.0%

: 107515-10-6
(3S,4R)-1-<<(allyloxy)carbonyl>(triphenylphosphoranylidene)methyl>-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<4'-(azidomethyl)phenyl>carbonyl>ethyl>azetidin-2-one

: 107515-16-2
allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

Guidance literature:: In xylene; at 130 ℃; for 6h;
DOI:10.1021/jm00388a022

Reference yield:

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

: 107515-16-2
allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 10 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

9: 85 percent / LiN₃ / dimethylformamide / 2 h / Ambient temperature

10: 71 percent / xylene / 6 h / 130 °C

With pyridine; thionyl chloride; lithium azide; tetrabutyl ammonium fluoride; acetic acid; periodic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; xylene;
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

: 107515-16-2
allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 10 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

9: 85 percent / LiN₃ / dimethylformamide / 2 h / Ambient temperature

10: 71 percent / xylene / 6 h / 130 °C

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