4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R)-

Base Information

• Chemical Name: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R)-
• CAS No.: 35564-99-9
• Molecular Formula: C15H15Br2NO3S
• Molecular Weight: 449.163
• Mol file: 35564-99-9.mol

Synonyms:benzyl 6,6-dibromopenicillinate;6,6-dibromopenicillanic acid benzyl ester;(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester;Benzyl-6,6-Dibromopenicillanate;(2S,5R)-benzyloxycarbonyl-6,6-dibromo-7-oxo-1-thia-4-azabicyclo<3.2.0>heptane;benzyl 6,6-dibromo-2,2-dimethyl-(5R)penam-3α-carboxylate;6,6-dibromo-penicillanic acid benzyl ester;

Chemical Property of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R)-

Chemical Property:

• PSA: 71.91000
• LogP: 3.21610

Purity/Quality:

Benzyl6,6-Dibromopenicillanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R)-

There total 10 articles about 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6,6-dibromo-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R)- 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%

benzyl bromide (100-39-0) + 6,6-dibromopenicillanic acid (24158-88-1) → benzyl 6,6-dibromopenicillanate (35564-99-9)

Guidance literature:

With triethylamine; In ice-water; N,N-dimethyl acetamide;

Reference yield: 89.0%

benzyl chloride (100-44-7) + 6,6-dibromopenicillanic acid (24158-88-1) → benzyl 6,6-dibromopenicillanate (35564-99-9)

Guidance literature:

With dmap; tetra-(n-butyl)ammonium iodide; triethylamine; In chloroform; for 24h; Inert atmosphere; Reflux;

DOI:10.1039/c4md00430b

Reference yield: 85.0%

benzyl bromide (100-39-0) + 6,6-dibromopenicillanic acid (24158-88-1) → benzyl 6,6-dibromo-2,2-dimethyl-(5R)penam-3α-carboxylate (35564-99-9)

Guidance literature:

With triethylamine; In ice-water; N,N-dimethyl acetamide; ethyl acetate;

upstream raw materials:

benzyl alcohol

benzyl bromide

6,6-dibromopenicillanic acid

6,6-dibromopenicillanic acid

Downstream raw materials:

(5R)-6c-bromo-6t-((R)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester

(5R)-6t-bromo-6c-((Ξ)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester

benzyl 6-bromo-6-(2-phenylsulphinyl-2-ethoxycarbonylethyl)penicillanate

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