(6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: (6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 87314-56-5
• Molecular Formula: C₁₆H₁₇N₃O₃S
• Molecular Weight: 331.395
• DSSTox Substance ID: DTXSID70521030
• Wikidata: Q72436397
• Mol file: 87314-56-5.mol

Synonyms:87314-56-5;(6R,7R)-7-amino-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;(6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;(6R,7R)-7-Amino-3-[(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;DTXSID70521030

Chemical Property of (6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• PSA: 90.34000
• LogP: -0.56310
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 331.09906259
• Heavy Atom Count: 23
• Complexity: 573

Purity/Quality:

99% ^*data from raw suppliers

(6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C1)[N+](=CC=C2)CC3=C(N4C(C(C4=O)N)SC3)C(=O)[O-]
• Isomeric SMILES: C1CC2=C(C1)[N+](=CC=C2)CC3=C(N4[C@@H]([C@@H](C4=O)N)SC3)C(=O)[O-]

Technology Process of (6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 4 articles about (6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 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:

C24H23N3O4S (95055-53-1) → 7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate (87314-56-5)

Guidance literature:

With penicillin G acylase; In water; at 37 ℃; pH=8 - 8.5; aq. acetate buffer; Enzymatic reaction;

DOI:10.1080/00397911003629499

Reference yield:

p-methoxybenzyl 7-phenylacetamido-3-(2,3-cyclopenteno-1-pyridinio)-3-cephem-4-carboxylate iodide (1273319-61-1) → 7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate (87314-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: phenol / 4.5 h / 50 °C

2: penicillin G acylase / water / 37 °C / pH 8 - 8.5 / aq. acetate buffer; Enzymatic reaction

With penicillin G acylase; phenol; In water;

DOI:10.1080/00397911003629499

Reference yield:

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (104146-10-3) → 7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate (87314-56-5)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium iodide / acetone / 5 h / -5 - 0 °C / Darkness; Inert atmosphere

2: ethyl acetate / -5 °C / Inert atmosphere

3: phenol / 4.5 h / 50 °C

4: penicillin G acylase / water / 37 °C / pH 8 - 8.5 / aq. acetate buffer; Enzymatic reaction

With penicillin G acylase; sodium iodide; phenol; In water; ethyl acetate; acetone;

DOI:10.1080/00397911003629499

upstream raw materials:

p-methoxybenzyl 7-phenylacetamido-3-(2,3-cyclopenteno-1-pyridinio)-3-cephem-4-carboxylate iodide

C₂₄H₂₃N₃O₄S

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

(6R,7R)-4-methoxybenzyl-3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Refernces