(1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
• CAS No.: 847671-89-0
• Molecular Formula: C₂₈H₃₈N₂O₁₀S
• Molecular Weight: 594.683

Synonyms:(1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Chemical Property of (1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

There total 8 articles about (1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl 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: 95.0%

4-[2-acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-5-acetoxymethyl-3-oxo-2-(4-trimethylsilanyl-but-2-enyl)-3,4-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester (847671-88-9) → (1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (847671-89-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1039/b415030a

Reference yield:

(E)-(S)-2-tert-Butoxycarbonylamino-hex-4-enoic acid → (1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (847671-89-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 2,2,2-trifluoro-ethanol / 20 - 50 °C

2: t-BuOK; 4 Angstroem molecular sieves / tetrahydrofuran / 0 °C

3: aq. NaBH₄ / tetrahydrofuran

4: TBAF / tetrahydrofuran / 50 °C

5: pyridine

6: 51 percent / Cl₂Ru(-N(Mes)CH₂CH₂(Mes)N-)=CH-C₆H₄-O-i-Pr(o) / CH₂Cl₂ / Heating

7: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

With pyridine; sodium tetrahydroborate; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; Hoveyda-Grubbs Catalyst II; In tetrahydrofuran; dichloromethane; 2,2,2-trifluoroethanol; 1: Ugi four-component condensation;

DOI:10.1039/b415030a

Reference yield:

2-but-2-enyl-4-[2-hydroxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-oxo-3,4-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester → (1S,5R,6S)-3-[(R)-2-Acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (847671-89-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: 51 percent / Cl₂Ru(-N(Mes)CH₂CH₂(Mes)N-)=CH-C₆H₄-O-i-Pr(o) / CH₂Cl₂ / Heating

3: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

With pyridine; boron trifluoride diethyl etherate; Hoveyda-Grubbs Catalyst II; In dichloromethane;

DOI:10.1039/b415030a

upstream raw materials:

4-[2-acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-5-acetoxymethyl-3-oxo-2-(4-trimethylsilanyl-but-2-enyl)-3,4-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester

4-[2-acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-5-acetoxymethyl-2-but-2-enyl-3-oxo-3,4-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester

methanesulfonic acid 6-[1-amino-2-(tert-butyldiphenylsilanyloxy)ethyl]-2,4-dimethoxy-3-methylphenyl ester

Downstream raw materials:

(1S,5R,6S)-3-[(R)-1-(2-Methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-methylene-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-hydroxymethyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

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