(2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

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Chemical Name:(2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
CAS No.:83162-14-5
Molecular Formula:C₂₃H₃₅NO₄SSi
Molecular Weight:449.687
Hs Code.:

Synonyms:(2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

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Chemical Property of (2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

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Technology Process of (2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 8 articles about (2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 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: 89.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 80951-80-0
benzyl 6-alpha-(1-hydroxyethyl)penicillanate

: 76855-65-7,80845-13-2,83162-14-5,83247-78-3
(2S,5R,6S)-6-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 5h; Ambient temperature;

Reference yield:

: 15058-70-5
6-diazopenicillanic acid benzyl ester

: 83162-14-5
(2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: BF₃*OEt₂ / CH₂Cl₂

2: BuLi / tetrahydrofuran / 0.67 h / -78 °C

3: 100 percent / Bu₃SnH / AIBN / tetrahydrofuran / 2 h / 60 °C

4: imidazole / dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; n-butyllithium; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.59.1887

Reference yield:

: 83212-60-6
benzyl (2S,5R,6S)-6-<(R)-1-hydroxyethyl>-6-(phenylseleno)penicillanate

: 83162-14-5
(2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / Bu₃SnH / AIBN / tetrahydrofuran / 2 h / 60 °C

2: imidazole / dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.59.1887