(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 15690-38-7
• Molecular Formula: C8H10N2O4S
• Molecular Weight: 230.244
• European Community (EC) Number: 239-787-2
• UNII: 57NLN1Y39I
• Nikkaji Number: J248.733K
• Wikidata: Q27261509
• Mol file: 15690-38-7.mol

Synonyms:15690-38-7;(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Deacetyl-7-aminocephalosporanic Acid;7-Amino-deacetylcephalosporanic Acid;(6R-trans)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;UNII-57NLN1Y39I;57NLN1Y39I;EINECS 239-787-2;MFCD09751258;(6R-trans)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;HACA;Hydroxymethyl-7-aminocephalosporanic acid;7-ADACA;3-Hydroxymethyl-7-aminoceph-3-em-4-carboxylic Acid;SCHEMBL3244823;BQIMPGFMMOZASS-CLZZGJSISA-N;AKOS016010512;CS-T-47682;DS-4854;CS-0058666;(+)-DEACETYL-7-AMINOCEPHALOSPORANIC ACID;EN300-6748554;A809785;Q27261509;7beta-amino-3-hydroxymethyl -3-cephem-4-carboxylic acid;7beta-amino-3-hydroxymethyl-3-cephem-4-carboxylic acid;Z1509564382;(6R,7R)-7-AMINO-3-HYDROXYMETHYLCEPH-3-EM-4-CARBOXYLIC ACID;7.BETA.-AMINO-3-(HYDROXYMETHYL)-3-CEPHEM-4-CARBOXYLIC ACID;(2S)-N-[(1S,3R)-3-acetamido-1-[[(2S)-2-[[(2R)-6-amino-2-[[(2S)-3-(4-hydroxyphenyl)-2-(methylamino)propanoyl]amino]hexanoyl]amino]-4-methyl-pentanoyl]-[(2S)-2-[[(2R)-2-amino-3-(3-pyridyl)propanoyl]amino]-3-hydroxy-propanoyl]carbamoyl]-1-methyl-4-(2-naphthy;7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-3-(HYDROXYMETHYL)-8-OXO-, (6R,7R)-;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-amino-3-(hydroxymethyl)-8-oxo-, (6R-trans)-

Chemical Property of (6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 7.46E-18mmHg at 25°C
• Refractive Index: 1.742
• Boiling Point: 617.905 °C at 760 mmHg
• PKA: 2.68±0.50(Predicted)
• Flash Point: 327.498 °C
• PSA: 129.16000
• Density: 1.749 g/cm³
• LogP: -0.80200
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -4.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 230.03612798
• Heavy Atom Count: 15
• Complexity: 368

Purity/Quality:

99.9% ^*data from raw suppliers

7-Amino-deacetylcephalosporanicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(N2C(S1)C(C2=O)N)C(=O)O)CO
• Isomeric SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)N)C(=O)O)CO
• Uses: Intermediate in the semi-synthetic cephalosporins synthesis. Found in Acremonium chrysogenum.

Technology Process of (6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 2 articles about (6R,7R)-7-Amino-3-(hydroxymethyl)-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: 90.1%

7-Aminocephalosporanic acid (957-68-6) → (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydroxide; In methanol; water; at -5 - 5 ℃;

Reference yield:

cephalosporin C (909885-59-2) → deacetylcephalosporin C (1476-46-6,51921-09-6,128109-36-4) + deacetylglutaryl-7-amino-caphalosporanic acid (55779-10-7) + (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0.]oct-2-ene-2-carboxylic acid (15690-38-7)

Guidance literature:

With carbon dioxide; water; degradation of cephalosporin C by lytic enzymes from autolysed cultures of filamentous fungi;

DOI:10.1111/j.2042-7158.1990.tb05368.x

Reference yield: 89.1%

(Z)-2-methoxyimino-2-(furyl-2-yl)acetic acid ammonium salt (97148-39-5) + (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → (6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (56271-94-4)

Guidance literature:

(Z)-2-methoxyimino-2-(furyl-2-yl)acetic acid ammonium salt; With N,N-dimethyl acetamide; phosphorus pentachloride; In dichloromethane; at -30 - -10 ℃; for 1.33333h;

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With sodium hydroxide; In dichloromethane; water; for 2h; pH=6.5 - 7;

upstream raw materials:

cephalosporin C

7-Aminocephalosporanic acid

Downstream raw materials:

(6R)-3-hydroxymethyl-8-oxo-7t-((R)-2-phenyl-2-sulfo-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

cefalexin

C₂₀H₁₉N₃O₄S

3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 Coene, Bernard,Schanck, Andre,Dereppe, Jean-Marie,Meerssche, Maurice Van. "Substituent Effects on Reactivity and Spectral Parameters of Cephalosporins". . p. 694 - 700. Retrieved 1984.
• 2、 -. "FLUOROGENIC BETA-LACTAMASE SUBSTRATE AND ASSOCIATED DETECTION METHOD". Page/Page column 40; 42-43. . Retrieved 2021/06/04.
• 3、 -. "A hydrochloric acid Cefcapene pivoxil preparation method". Paragraph 0041-0042. . Retrieved 2018/06/19.