(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester

Base Information

• Chemical Name: (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester
• CAS No.: 149809-43-8
• Molecular Formula: C21H21F2N3O4S
• Molecular Weight: 449.478
• UNII: LDY4QZP8PB
• DSSTox Substance ID: DTXSID70447488
• Nikkaji Number: J760.533A
• Wikidata: Q72509236
• Mol file: 149809-43-8.mol

Synonyms:149809-43-8;(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester;LDY4QZP8PB;[(3S,5R)-5-(2,4-DIFLUOROPHENYL)-5-(1,2,4-TRIAZOL-1-YLMETHYL)OXOLAN-3-YL]METHYL 4-METHYLBENZENESULFONATE;((3S,5R)-5-((1H-1,2,4-triazol-1-yl)Methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)Methyl 4-Methylbenzenesulfonate;((3S,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)-tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate;2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol;(5R-cis)-Toluene-4-sulfonic Acid 5-(2,4-Difluorophenyl)-5-[1,2,4]triazol-1-ylmethyltetrahydrofuran-3-ylmethyl Ester;(5R-cis)-Toluene-4-sulfonic Acid 5-(2,4-Difluorophenyl)-5-[1,2,4]triazol-1-ylmethyltetrahydrofuran-3;D-Threo-pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-((((4-methylphenyl)sulfonyl)oxy)methyl)-1-(1H-1,2,4-triazol-1-yl)-;D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-;2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-((((4-methylphenyl)sulfonyl)oxy)methyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol;UNII-LDY4QZP8PB;SCHEMBL12067228;DTXSID70447488;DFWVLCJRFGIRAK-KKSFZXQISA-N;(3S,5R)-5-(2,4-Difluorophenyl)-5-[(1H-1,2,4-triazol-1-yl)methyl]oxolan-3-ylmethyl p-Toluenesulfonate;CS-M2899;p-Toluenesulfonic Acid (3S,5R)-5-(2,4-Difluorophenyl)-5-[(1H-1,2,4-triazol-1-yl)methyl]oxolan-3-ylmethyl Ester;AKOS025402355;AC-8330;CS-O-31365;AS-47912;CID 10895629;1-ylmethyltetrahydrofuran-3-ylmethyl Ester;D4537;F16788;J-501622;(5R-cis)-Toluene-4-sulfonic Acid 5-(2,4-Difluorophenyl)-5-[1,2,4]triazol-;((3S,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluoro phenyl)tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate;((3S,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate;{(3S,5R)-5-(2,4-Difluorophenyl)-5-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran-3-yl}methyl 4-methylbenzenesulfonate;2,5-Anhydro-1,3,4-trideoxy-2-(2,4-difluorophenyl)-4-{[(4-methylbenzene-1-sulfonyl)oxy]methyl}-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol;p-Toluenesulfonic acid [5-(2,4-difluorophenyl)-5beta-(1H-1,2,4-triazol-1-ylmethyl)tetrahydrofuran]-3beta-ylmethyl ester

Chemical Property of (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester

Chemical Property:

• Vapor Pressure: 9.85E-15mmHg at 25°C
• Melting Point: 100-102°C
• Refractive Index: 1.615
• Boiling Point: 608.1 °C at 760 mmHg
• PKA: 2.75±0.10(Predicted)
• Flash Point: 321.6 °C
• PSA: 91.69000
• Density: 1.40 g/cm³
• LogP: 4.28300
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: slightly sol. in Chloroform
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 449.12208366
• Heavy Atom Count: 31
• Complexity: 701

Purity/Quality:

99% ^*data from raw suppliers

(5R-cis)-Toluene-4-sulfonicAcid5-(2,4-Difluorophenyl)-5-[1,2,4]triazol-1-ylmethyltetrahydrofuran-3-ylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2CC(OC2)(CN3C=NC=N3)C4=C(C=C(C=C4)F)F
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2C[C@](OC2)(CN3C=NC=N3)C4=C(C=C(C=C4)F)F
• Uses: Posaconazole intermediate. Antifungal agent. Posaconazole intermediate. Antifungal agent

Technology Process of (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester

There total 47 articles about (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester 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: 94.0%

C14H15F2N3O2*(x)ClH + p-toluenesulfonyl chloride (98-59-9) → (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran (149809-43-8)

Guidance literature:

C₁₄H₁₅F₂N₃O₂*(x)ClH; With triethylamine; In dichloromethane; at 12 - 22 ℃; for 1h;

p-toluenesulfonyl chloride; With dmap; In dichloromethane; at 12 - 25 ℃; for 4h;

Reference yield: 94.0%

C14H15F2N3O2*ClH (1350466-82-8) + p-toluenesulfonyl chloride (98-59-9) → (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran (149809-43-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 14 - 30 ℃;

Reference yield: 93.0%

p-toluenesulfonyl chloride (98-59-9) + ((3R,5R)-5-((1H-1,2,4-triazole-1-yl) methyl)-5-(2,4-difluorophenyl) tetrahydrofuran-3-yl)methanol (160709-02-4) → (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran (149809-43-8)

Guidance literature:

With dmap; In tetrahydrofuran; for 18h;

DOI:10.1016/0040-4039(94)88071-9

upstream raw materials:

p-toluenesulfonyl chloride

((3R,5R)-5-((1H-1,2,4-triazole-1-yl) methyl)-5-(2,4-difluorophenyl) tetrahydrofuran-3-yl)methanol

4-(2,4-Difluoro-phenyl)-pent-4-enoyl chloride

((3R,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydrofuran-3-yl)methanol

Downstream raw materials:

C₃₀H₃₂F₂N₆O₂

posaconazote

C₃₇H₄₄F₂N₈O₅

4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)-3-methylphenyl)piperazin-1-yl)-N-(4-fluorophenyl)benzamide

Refernces

• 1、 -. "POSACONAZOLE, COMPOSITION, INTERMEDIATE, PREPARATION METHOD THEREFOR, AND USES THEREOF". Paragraph 0246-0247. . Retrieved 2019/03/14.
• 2、 -. "IMPROVED PROCESS FOR THE PREPARATION OF ((3S,5R)-5-((1H-1,2,4-TRIAZOL-1-YL)METHYL)-5-(2,4-DIFLUOROPHENYL)TETRAHYDROFURAN-3-YL)METHYL-4-METHYLBENZENESULFONATE". Page/Page column 22. . Retrieved 2015/05/06.