6-β-phenylacetamidopenicillanic acid-(1S)-oxide

Base Information

• Chemical Name: 6-β-phenylacetamidopenicillanic acid-(1S)-oxide
• CAS No.: 54275-92-2
• Molecular Formula: C₂₃H₂₄N₂O₅S
• Molecular Weight: 440.52
• Mol file: 54275-92-2.mol

Synonyms:6-β-phenylacetamidopenicillanic acid-(1S)-oxide

Chemical Property of 6-β-phenylacetamidopenicillanic acid-(1S)-oxide

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of 6-β-phenylacetamidopenicillanic acid-(1S)-oxide

There total 1 articles about 6-β-phenylacetamidopenicillanic acid-(1S)-oxide 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:

Penicillin G sodium (69-57-8) + benzyl bromide (100-39-0) → 6-β-phenylacetamidopenicillanic acid-(1S)-oxide (54275-92-2)

Guidance literature:

With sodium periodate; Yield given. Multistep reaction; 1) H₂O; 2) NEt₃, DMF, 20 deg C;

DOI:10.1016/S0040-4020(01)92143-X

Reference yield: 58.0%

(2S,4S,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (4052-68-0,41399-37-5,54275-92-2,59751-76-7,59751-77-8,68000-32-8,73036-92-7) → (R)-2-((1S,5R)-3-Benzyl-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester (78037-14-6)

Guidance literature:

With triphenylphosphine; squaric acid; In N,N-dimethyl acetamide; 1,2-dichloro-ethane; toluene; for 6h; Heating;

DOI:10.1016/S0040-4039(01)81835-9

Reference yield: 32.0%

6-β-phenylacetamidopenicillanic acid-(1S)-oxide (54275-92-2) → 6-Deuteriobenzylpenicillin (S)-S-Oxide Benzyl Ester (76757-87-4) + C23H23(2)HN2O5S (76757-88-5)

Guidance literature:

With water-d2; triethylamine; In acetonitrile; at 22 ℃; for 24h;

DOI:10.1021/jo00323a013

upstream raw materials:

Penicillin G sodium

benzyl bromide

Downstream raw materials:

(R)-2-((1S,5R)-3-Benzyl-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester

6-Deuteriobenzylpenicillin (S)-S-Oxide Benzyl Ester

C₂₃H₂₃⁽²⁾HN₂O₅S

2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-enoic acid benzyl ester