(2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 345203-88-5
• Molecular Formula: C₂₄H₂₂BrNO₆S
• Molecular Weight: 532.412
• Mol file: 345203-88-5.mol

Synonyms:(2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 1 articles about (2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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: 61.0%

Propargylic aldehyde (624-67-9) + (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester (81324-43-8) → (2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-88-5)

Guidance literature:

With ethylmagnesium bromide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0960-894X(01)00148-2

Reference yield: 71.0%

(2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-88-5) → (2S,5R,6R)-6-(1-Hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-89-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃;

DOI:10.1016/S0960-894X(01)00148-2

Reference yield:

(2S,5R,6R)-6-Bromo-6-(1-hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-88-5) → (2S,5R,6R)-6-[1-(4-Fluoro-phenyl)-1H-[1,2,3]triazol-4-ylmethyl]-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / Bu₃SnH; AIBN / toluene / 80 °C

2: toluene / Heating

3: pyridine

4: 65 percent / H₂ / Pd/C / 3 h

With pyridine; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; palladium on activated charcoal; In toluene;

DOI:10.1016/S0960-894X(01)00148-2

upstream raw materials:

Propargylic aldehyde

(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

Downstream raw materials:

(2S,5R,6R)-6-(1-Hydroxy-prop-2-ynyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,5R,6R)-6-[Hydroxy-(1-phenyl-1H-[1,2,3]triazol-4-yl)-methyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,5R,6R)-6-{[1-(4-Fluoro-phenyl)-1H-[1,2,3]triazol-4-yl]-hydroxy-methyl}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,5R,6R)-6-{[1-(4-Amino-phenyl)-1H-[1,2,3]triazol-4-yl]-hydroxy-methyl}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester