allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex

Base Information

Chemical Name:allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex
CAS No.:107515-24-2
Molecular Formula:C₂₀H₂₂N₄O₄
Molecular Weight:382.419
Hs Code.:

Synonyms:allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex

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Chemical Property of allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex

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Technology Process of allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex

There total 13 articles about allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex 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: 44.0%

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

: 107515-24-2
allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 40h; Ambient temperature;
DOI:10.1021/jm00388a022

Reference yield:

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

: 107515-24-2
allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex

Guidance literature:: Multi-step reaction with 11 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

11: 44 percent / glacial acetic acid, tetra-n-butylammonium fluoride / tetrahydrofuran / 40 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; 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

: 107515-24-2
allyl (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylatex

Guidance literature:: Multi-step reaction with 11 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

11: 44 percent / glacial acetic acid, tetra-n-butylammonium fluoride / tetrahydrofuran / 40 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; xylene;
DOI:10.1021/jm00388a022