(6R-(6alpha,7beta(R*)))-3-(Acetoxymethyl)-7-((formyloxy)phenylacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (6R-(6alpha,7beta(R*)))-3-(Acetoxymethyl)-7-((formyloxy)phenylacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• CAS No.: 87932-78-3
• Molecular Formula: C19H18 N2 O8 S
• Molecular Weight: 434.427
• European Community (EC) Number: 289-358-9
• DSSTox Substance ID: DTXSID40236700
• Nikkaji Number: J334.025B
• Wikidata: Q76390091
• Mol file: 87932-78-3.mol

Synonyms:87932-78-3;EINECS 289-358-9;(6R-(6alpha,7beta(R*)))-3-(Acetoxymethyl)-7-((formyloxy)phenylacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;(6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-formyloxy-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;[6R-[6alpha,7beta(R*)]]-3-(acetoxymethyl)-7-[(formyloxy)phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(formyloxy)phenylacetyl]amino]-8-oxo-, [6R-[6alpha,7beta(R*)]]-;C19H18N2O8S;DTXSID40236700;C19-H18-N2-O8-S;(7R)-3-[(Acetyloxy)methyl]-7-[[(R)-(formyloxy)phenylacetyl]amino]cepham-3-ene-4-carboxylic acid

Chemical Property of (6R-(6alpha,7beta(R*)))-3-(Acetoxymethyl)-7-((formyloxy)phenylacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Chemical Property:

• PSA: 168.10000
• LogP: 1.61650
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 434.07838671
• Heavy Atom Count: 30
• Complexity: 777

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)OC=O)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)OC=O)SC1)C(=O)O

Technology Process of (6R-(6alpha,7beta(R*)))-3-(Acetoxymethyl)-7-((formyloxy)phenylacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

There total 2 articles about (6R-(6alpha,7beta(R*)))-3-(Acetoxymethyl)-7-((formyloxy)phenylacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-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:

(R)-formiloxy(phenyl)acetic acid (29169-63-9) → (2'R,6R,7R)-3-acetoxymethyl-7-formyloxy(phenyl)acetylaminoceph-3-em-4-carboxylic acid (87932-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride, dimethylformamide / Heating

2: acetone; H₂O / 4 h / Ambient temperature

With thionyl chloride; N,N-dimethyl-formamide; In water; acetone;

Reference yield:

D-2-phenyl-2-formyloxyacetyl chloride (29169-64-0) + 7-Aminocephalosporanic acid (957-68-6) → (2'R,6R,7R)-3-acetoxymethyl-7-formyloxy(phenyl)acetylaminoceph-3-em-4-carboxylic acid (87932-78-3)

Guidance literature:

In water; acetone; for 4h; Yield given; Ambient temperature;

Reference yield:

(2'R,6R,7R)-3-acetoxymethyl-7-formyloxy(phenyl)acetylaminoceph-3-em-4-carboxylic acid (87932-78-3) → 7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ3-cephem-4-carboxylic acid (51818-85-0)

Guidance literature:

With potassium hydrogencarbonate; In methanol; for 5h; Ambient temperature;

upstream raw materials:

D-2-phenyl-2-formyloxyacetyl chloride

7-Aminocephalosporanic acid

(R)-formiloxy(phenyl)acetic acid

Downstream raw materials:

7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ³-cephem-4-carboxylic acid

(5'R,6R,7S)-3-acetoxymethyl-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylic acid

4-nitrobenzyl (5'R,6R,7S)-3-acetoxy-4'-oxo-5'-phenylspiro(1',3'-oxazolidine-2',7-ceph-3-em)-4-carboxylate

4-nitrobenzyl (2'R,6R,7R)-3-acetoxymethyl-7-hydroxy(phenyl)acetylaminoceph-3-em-4-carboxylate