ent-Voriconazole

Base Information

• Chemical Name: ent-Voriconazole
• CAS No.: 137234-63-0
• Molecular Formula: C16H14F3N5O
• Molecular Weight: 349.31
• Hs Code.: 2933997500
• UNII: 1Y58LNV43M
• DSSTox Substance ID: DTXSID60160114
• Wikidata: Q27253140
• Mol file: 137234-63-0.mol

Synonyms:ent-Voriconazole;137234-63-0;(2S,3R)-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;188416-29-7;Voriconazole enantiomer;(2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol;1Y58LNV43M;(2S,3R)-rel-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;(2R,3S/2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;C16H14F3N5O;UNII-1Y58LNV43M;Voriconazole specified impurity D [EP];EPI-VORICONAZOLE;SCHEMBL371715;DTXSID60160114;BCEHBSKCWLPMDN-HWPZZCPQSA-N;BCP11125;AKOS016844178;AC-8178;4-Pyrimidineethanol, alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-, (alphaS,betaR)-;DS-11148;VORICONAZOLE IMPURITY D [EP IMPURITY];D84333;EN300-7376311;A908151;Q27253140;(2R,3S/2S,3R)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyriMidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (RaceMic Voriconazole);(2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol;4-PYRIMIDINEETHANOL, .ALPHA.-(2,4-DIFLUOROPHENYL)-5-FLUORO-.BETA.-METHYL-.ALPHA.-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-, (.ALPHA.S,.BETA.R)-

Chemical Property of ent-Voriconazole

Chemical Property:

• Melting Point: 130-132°C
• Boiling Point: 508.6±60.0 °C(Predicted)
• PKA: 11.54±0.29(Predicted)
• PSA: 76.72000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 2.17690
• Storage Temp.: -20?C Freezer
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 349.11504457
• Heavy Atom Count: 25
• Complexity: 448

Purity/Quality:

99% ^*data from raw suppliers

ent-Voriconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
• Isomeric SMILES: C[C@H](C1=NC=NC=C1F)[C@@](CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
• Uses: The (2S,3R) enantiomer in Voriconazole (V760000) drug substance.

Technology Process of ent-Voriconazole

There total 156 articles about ent-Voriconazole 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: 92.5%

(2R,3S/2S,3R)-6-[4-(3,5-dibromo-1H-1,2,4-triazol-1-yl)-3-(2,4-difluorophenyl)-3-hydroxybutan-2-yl]-5-fluoropyrimidin-4-yl methanesulfonate → 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (182230-43-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

With ammonium formate; palladium on carbon; In toluene; at 80 ℃; for 3h;

Reference yield: 92.0%

2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol (137234-63-0,173967-54-9,188416-29-7) → voriconazole (137234-62-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol; With (1S)-10-camphorsulfonic acid; In methanol; acetone; for 1h; Reflux;

With sodium hydroxide; In dichloromethane; water; pH=11 - 12;

Reference yield: 86.3%

C26H28F3N5O5S → voriconazole (137234-62-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; under 760.051 Torr;

upstream raw materials:

2-fluoro-3-oxopentanoic acid ethyl ester

6-Ethyl-5-fluoropyrimidin-4(3H)-one

4-chloro-6-ethyl-5-fluoropyrimidine

1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Downstream raw materials:

C₁₆H₁₄F₃N₅O*C₇H₆O₃

C₁₆H₁₄F₃N₅O*C₇H₇NO₂

C₁₆H₁₄F₃N₅O*C₇H₅NO₄

Refernces

• 1、 -. "Synthesis method of voriconazole and intermediate of voriconazole". Paragraph 0049; 0053-0058. . Retrieved 2020/02/14.
• 2、 -. "Voriconazole synthesis method". . . Retrieved 2020/08/02.