Carbapenem-3-carboxylic acid

Base Information

• Chemical Name: Carbapenem-3-carboxylic acid
• CAS No.: 78854-41-8
• Deprecated CAS: 82768-37-4
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.137
• UNII: GL970841YS
• DSSTox Substance ID: DTXSID401192165
• Nikkaji Number: J1.466.424F
• Wikidata: Q27105319
• Metabolomics Workbench ID: 52816
• ChEMBL ID: CHEMBL1240705
• Mol file: 78854-41-8.mol

Synonyms:carbapenem-3-carboxylic acid;SQ 27,860;SQ 27860;SQ-27,860;SQ-27860

Chemical Property of Carbapenem-3-carboxylic acid

Chemical Property:

• PSA: 57.61000
• LogP: -0.10260
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 153.042593085
• Heavy Atom Count: 11
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=C(N2C1CC2=O)C(=O)O
• Isomeric SMILES: C1C=C(N2[C@H]1CC2=O)C(=O)O

Technology Process of Carbapenem-3-carboxylic acid

There total 5 articles about Carbapenem-3-carboxylic acid 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: 62.0%

→ carbapenem (82768-37-4,83200-96-8,78854-41-8)

Guidance literature:

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + acetic acid (64-19-7,77671-22-8) → (5R)-carbapenem-3-carboxylic acid (78854-41-8) + (3S,5R)-carbapenam (112419-10-0,807613-68-9,112283-40-6) + (3S,5S)-carbapenam (112419-10-0,807613-68-9,112283-40-6)

Guidance literature:

With carABC plasmid from Erwinia carotovora; LB medium; pET₂₄a; In water; at 28 ℃; for 5h;

DOI:10.1021/ja001723l

Reference yield:

(2S,5S)-trans-5-carboxymethylproline (176036-37-6) → (5R)-carbapenem-3-carboxylic acid (78854-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: ATP; magnesium(II) / Enzymatic reaction

2: Pectobacterium carotovorum; oxygen; non-heme iron oxygenase; carbapenam synthase; α-ketoglutarate / Enzymatic reaction

With α-ketoglutarate; carbapenam synthase; non-heme iron oxygenase; Pectobacterium carotovorum; magnesium(II); oxygen; ATP;

DOI:10.1021/ja311078s

upstream raw materials:

L-glutamic acid

acetic acid

(3S,5S)-carbapenam

(3S,5R)-carbapenam

Refernces

A short formal synthesis of the carbapenem antibiotic (±)-PS-5

10.1039/c39880000809

The study presents a practical stereoselective synthesis of 4-acetoxy-3-ethylazetidin-2-one, a key intermediate for the carbapenem antibiotic (+)-PS-5, using a Reformatsky reaction between methyl-a-bromo butyrate and N-4-methoxyp henyl-a-methylcin namylideneamine. The authors explored different conditions and reagents, finding that using toluene instead of benzene increased the yield and stereoselectivity of the reaction. The synthesized intermediate was then subjected to ozonolysis and Baeyer-Villiger oxidation to introduce the required 4-acetoxy group. The final step involved removing the N-aryl substituent using cerium(iv) ammonium nitrate (CAN) to obtain the desired product. The study also demonstrated the versatility of this method by synthesizing other functionalized β-lactams, highlighting the potential for creating a wide range of 3-alkyl side chain β-lactams using readily available and inexpensive starting materials.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 78854-41-8 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid,7-oxo-,(5R)-(9CI)

Send

Send

Metric Ton KG G Pound L ML

Send

Send