(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
• CAS No.: 85253-93-6
• Molecular Formula: C₂₃H₃₅NO₆SSi
• Molecular Weight: 481.686

Synonyms:(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property of (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 15 articles about (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-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:

6-diazopenicillanic acid benzyl ester (15058-70-5) → (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (85253-93-6)

Guidance literature:

Multi-step reaction with 6 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

5: m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 1 h / 20 - 25 °C

With 1H-imidazole; n-butyllithium; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; 2,2'-azobis(isobutyronitrile); DBN; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.59.1887

Reference yield:

(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 (83162-14-5) → (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (85253-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

2: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 1 h / 20 - 25 °C

With 3-chloro-benzenecarboperoxoic acid; DBN; In dichloromethane;

DOI:10.1246/bcsj.59.1887

Reference yield:

benzyl (2S,5R,6S)-6-<(R)-1-hydroxyethyl>-6-(phenylseleno)penicillanate (83212-60-6) → (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (85253-93-6)

Guidance literature:

Multi-step reaction with 4 steps

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

2: imidazole / dimethylformamide / 20 h / Ambient temperature

3: m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

4: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 1 h / 20 - 25 °C

With 1H-imidazole; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; 2,2'-azobis(isobutyronitrile); DBN; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.59.1887

upstream raw materials:

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

tert-butyldimethylsilyl chloride

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

(S)-3,3-Dimethyl-7-oxo-6,6-bis-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Downstream raw materials:

(2S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone

benzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-methylsulfonyl-2-oxo-1-azetidinyl>-3-methyl-2-butenoate

(3S,4R)-4-benzenesulfonyl-3-((1R)-1-(tert-butyldimethylsilanyloxy)-ethyl)-azetidin-2-one

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