(6R,7R)

Base Information

• Chemical Name: (6R,7R)
• CAS No.: 112953-21-6
• Molecular Formula: C₃₄H₂₉N₃O₄S₂
• Molecular Weight: 607.754
• Mol file: 112953-21-6.mol

Synonyms:(6R,7R)-7-Phenylacetamido-3-[(Z)-2-(4-methylthiazol-5-yl)ethenyl]-3-cephem-4-carboxylic Acid Diphenyl Methyl Ester;(6R,7R)-7-Phenylacetamido-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenyl Methyl Ester;Diphenylmethyl (6R,7R)-3-<(Z)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate;7-phenylacetamido-3-[(Z)-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid diphenylmethyl ester;[6R-[3(Z),6|A,7|A]]-3-[2-(4-Methyl-5-thiazolyl)ethenyl]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl Ester;

Chemical Property of (6R,7R)

Chemical Property:

• PSA: 145.63000
• LogP: 6.47240

Purity/Quality:

97% ^*data from raw suppliers

(6R,7R)-7-Phenylacetamido-3-[(Z)-2-(4-methylthiazol-5-yl)ethenyl]-3-cephem-4-carboxylicAcidDiphenylMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Cephalosporin antibiotics and derivatives.

Technology Process of (6R,7R)

There total 2 articles about (6R,7R) 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:

4-(diphenylmethoxycarbonyl)-7β-phenylacetamidoceph-3-en-3-ylmethylphosphonium iodide (107550-89-0) → Diphenylmethyl (6R,7R)-3-<(Z)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate (112953-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 10percent aq. sodium carbonate / CH₂Cl₂ / 2 h

2: aq. sodium hydrogen carbonate / CH₂Cl₂ / 24 h

With sodium hydrogencarbonate; sodium carbonate; In dichloromethane;

Reference yield:

4-methyl-1,3-thiazole-5-carbaldehyde (82294-70-0) + cephalosporin 3'-triphenylphosphonium ylide (91439-21-3) → Diphenylmethyl (6R,7R)-3-<(Z)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate (112953-21-6) + Diphenylmethyl (6R,7R)-3-<(E)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate (135299-73-9)

Guidance literature:

With sodium hydrogencarbonate; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

Diphenylmethyl (6R,7R)-3-<(Z)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate (112953-21-6) + Diphenylmethyl (6R,7R)-3-<(E)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate (135299-73-9) → C21H18N3O4S2(1-)*Na(1+) + C21H18N3O4S2(1-)*Na(1+)

Guidance literature:

Diphenylmethyl (6R,7R)-3-<(Z)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate; Diphenylmethyl (6R,7R)-3-<(E)-2-(4-Methyl-1,3-thiazol-5-yl)vinyl>-7-phenylacetamidoceph-3-em-4-carboxylate; With phenol; at 50 - 55 ℃; for 5h;

With sodium hydrogencarbonate; In water; ethyl acetate; at 10 ℃; Product distribution / selectivity;

upstream raw materials:

4-methyl-1,3-thiazole-5-carbaldehyde

cephalosporin 3'-triphenylphosphonium ylide

4-(diphenylmethoxycarbonyl)-7β-phenylacetamidoceph-3-en-3-ylmethylphosphonium iodide

Downstream raw materials:

7-phenylacetamido-3-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid

Refernces