4-[4-[4-[4-[[(3r,5r)-5-(2,4-Difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2s,3s)-2-phenylmethoxypentan-3-yl]-1,2,4-triazol-3-one

Base Information

• Chemical Name: 4-[4-[4-[4-[[(3r,5r)-5-(2,4-Difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2s,3s)-2-phenylmethoxypentan-3-yl]-1,2,4-triazol-3-one
• CAS No.: 170985-86-1
• Molecular Formula: C44H48F2N8O4
• Molecular Weight: 790.913
• UNII: KP42ZUV3Z5
• DSSTox Substance ID: DTXSID70456434
• Wikidata: Q76416697
• Mol file: 170985-86-1.mol

Synonyms:O-Benzyl Posaconazole;170985-86-1;4-[4-[4-[4-[[(3r,5r)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2s,3s)-2-phenylmethoxypentan-3-yl]-1,2,4-triazol-3-one;KP42ZUV3Z5;CID 11136519;2-[(1S,2S)-2-(BENZYLOXY)-1-ETHYLPROPYL]-4-{4-[4-(4-{[(3R,5R)-5-(2,4-DIFLUOROPHENYL)-5-(1H-1,2,4-TRIAZOL-1-YLMETHYL)TETRAHYDROFURAN-3-YL]METHOXY}PHENYL)PIPERAZIN-1-YL]PHENYL}-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE;2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-((4-(4-(4-(1-((1S,2S)-1-ethyl-2-(phenylmethoxy)propyl)-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl)phenyl)-1-piperazinyl)phenoxy)methyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol;4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-Triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-((2S,3S)-2-(benzyloxy)pentan-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one;D-Threo-pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-((4-(4-(4-(1-((1S,2S)-1-ethyl-2-(phenylmethoxy)propyl)-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl)phenyl)-1-piperazinyl)phenoxy)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-[4-[4-[1-[(1S,2S)-1-ethyl-2-(phenylMethoxy)propyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]Methyl]-1-(1H-1,2,4-triazol-1-yl)-;yl)-D-threo-pentitol;UNII-KP42ZUV3Z5;SCHEMBL12068529;DTXSID70456434;XZBSQKGAKKWACB-QCKBNUSDSA-N;AMY30911;AKOS030254755;CS-T-49044;2,5-Anhydro-4-({4-[4-(4-{1-[(2S,3S)-2-(benzyloxy)pentan-3-yl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl}phenyl)piperazin-1-yl]phenoxy}methyl)-1,3,4-trideoxy-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol;4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluoro phenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one;D-threo-Pentitol,2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-(phenylMethoxy)propyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]Methyl]-1-(1H-1,2,4-triazol-1-yl)-

Chemical Property of 4-[4-[4-[4-[[(3r,5r)-5-(2,4-Difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2s,3s)-2-phenylmethoxypentan-3-yl]-1,2,4-triazol-3-one

Chemical Property:

• Boiling Point: 889.9±75.0 °C(Predicted)
• PKA: 6.49±0.40(Predicted)
• PSA: 104.70000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 7.07020
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 15
• Exact Mass: 790.37665837
• Heavy Atom Count: 58
• Complexity: 1320

Purity/Quality:

98%min ^*data from raw suppliers

O-BenzylPosaconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(C)OCC1=CC=CC=C1)N2C(=O)N(C=N2)C3=CC=C(C=C3)N4CCN(CC4)C5=CC=C(C=C5)OCC6CC(OC6)(CN7C=NC=N7)C8=C(C=C(C=C8)F)F
• Isomeric SMILES: CC[C@@H]([C@H](C)OCC1=CC=CC=C1)N2C(=O)N(C=N2)C3=CC=C(C=C3)N4CCN(CC4)C5=CC=C(C=C5)OC[C@H]6C[C@](OC6)(CN7C=NC=N7)C8=C(C=C(C=C8)F)F
• Uses: Precursor to the fungicide, Posaconazole.

Technology Process of 4-[4-[4-[4-[[(3r,5r)-5-(2,4-Difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2s,3s)-2-phenylmethoxypentan-3-yl]-1,2,4-triazol-3-one

There total 49 articles about 4-[4-[4-[4-[[(3r,5r)-5-(2,4-Difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2s,3s)-2-phenylmethoxypentan-3-yl]-1,2,4-triazol-3-one 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: 100.0%

2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one (184177-83-1) + (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran (149809-43-8) → 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one (170985-86-1)

Guidance literature:

(2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran; With sodium hydroxide; In dimethyl sulfoxide; for 0.166667h; Large scale;

2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one; In dimethyl sulfoxide; at 35 - 40 ℃; for 20h; Large scale;

Reference yield: 85.0%

2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one (184177-83-1) + C20H19F2N3O4S → 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one (170985-86-1)

Guidance literature:

2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one; With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 0.75h;

C₂₀H₁₉F₂N₃O₄S; In dimethyl sulfoxide; at 50 ℃; for 5h;

Reference yield: 85.0%

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide (170985-85-0) + [4-(4-{4-[(3R,5R)-5-(2,4-Difluoro-phenyl)-5-[1,2,4]triazol-1-ylmethyl-tetrahydro-furan-3-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-carbamic acid phenyl ester → 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one (170985-86-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene;

DOI:10.1016/j.tetlet.2004.09.028

upstream raw materials:

1-[(2R,4R)-4-(4-Bromo-phenoxymethyl)-2-(2,4-difluoro-phenyl)-tetrahydro-furan-2-ylmethyl]-1H-[1,2,4]triazole

2-((1S,2S)-2-Benzyloxy-1-ethyl-propyl)-4-(4-piperazin-1-yl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

4-bromo-phenol

Downstream raw materials:

posaconazote

Refernces

• 1、 -. "Preparation method of posaconazole". Paragraph 0066-0074. . Retrieved 2020/09/30.
• 2、 -. "POSACONAZOLE, COMPOSITION, INTERMEDIATE, PREPARATION METHOD THEREFOR, AND USES THEREOF". Paragraph 0248-0249. . Retrieved 2019/03/14.