(R)-2-Hydroxymethyl-4-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,4-pentanediol

Base Information

• Chemical Name: (R)-2-Hydroxymethyl-4-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,4-pentanediol
• CAS No.: 149809-38-1
• Molecular Formula: C₁₄H₁₇F₂N₃O₃
• Molecular Weight: 313.304
• DSSTox Substance ID: DTXSID201124944
• Nikkaji Number: J914.757H
• Mol file: 149809-38-1.mol

Synonyms:SCHEMBL6942089;DTXSID201124944;(R)-2-Hydroxymethyl-4-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,4-pentanediol;(4R)-4-(2,4-Difluorophenyl)-2-(hydroxymethyl)-5-(1H-1,2,4-triazol-1-yl)-1,4-pentanediol;149809-38-1

Chemical Property of (R)-2-Hydroxymethyl-4-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,4-pentanediol

Chemical Property:

• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 313.12379774
• Heavy Atom Count: 22
• Complexity: 349

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1F)F)C(CC(CO)CO)(CN2C=NC=N2)O
• Isomeric SMILES: C1=CC(=C(C=C1F)F)[C@](CC(CO)CO)(CN2C=NC=N2)O

Technology Process of (R)-2-Hydroxymethyl-4-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,4-pentanediol

There total 8 articles about (R)-2-Hydroxymethyl-4-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,4-pentanediol 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: 85.0%

C15H13F2N3O4 → (R)-4-(2,4-Difluoro-phenyl)-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentane-1,4-diol (149809-38-1)

Guidance literature:

With sodium tetrahydroborate; bromine; In tetrahydrofuran; methanol; at 20 - 60 ℃; for 1h; Reagent/catalyst;

Reference yield: 59.2%

Butyric acid (R)-2-butyryloxymethyl-4-(2,4-difluoro-phenyl)-4-hydroxy-5-[1,2,4]triazol-1-yl-pentyl ester (195509-58-1) → (R)-4-(2,4-Difluoro-phenyl)-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentane-1,4-diol (149809-38-1) + Butyric acid (2S,4R)-4-(2,4-difluoro-phenyl)-4-hydroxy-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentyl ester

Guidance literature:

With sodium hydroxide; Amano Lipase AK (Pseudomonas sp.); potassium chloride; In tetrahydrofuran; for 25h;

DOI:10.1021/jo9709920

Reference yield:

1-(1-Bromomethyl-vinyl)-2,4-difluoro-benzene (159276-58-1) → (R)-4-(2,4-Difluoro-phenyl)-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentane-1,4-diol (149809-38-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 20 °C

1.2: 1 h / 20 °C

2.1: C₂₈H₁₉O₂^(1-)*Fe⁽¹⁺⁾ / dichloromethane / 50 - 60 °C

3.1: sodium hydride / methanol; tetrahydrofuran / 1 h / 20 °C

3.2: Reflux

4.1: sodium tetrahydroborate; bromine / methanol; tetrahydrofuran / 1 h / 20 - 60 °C

With sodium tetrahydroborate; potassium tert-butylate; bromine; C₂₈H₁₉O₂^(1-)*Fe⁽¹⁺⁾; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

Acetic acid (R)-2-acetoxymethyl-4-(2,4-difluoro-phenyl)-4-hydroxy-5-[1,2,4]triazol-1-yl-pentyl ester

Butyric acid (R)-2-butyryloxymethyl-4-(2,4-difluoro-phenyl)-4-hydroxy-5-[1,2,4]triazol-1-yl-pentyl ester

1-(1-Bromomethyl-vinyl)-2,4-difluoro-benzene

1-(2-(2,4-difluorophenyl)allyl)-1H-1,2,4-triazole

Downstream raw materials:

Acetic acid (2R,4R)-4-(2,4-difluoro-phenyl)-4-hydroxy-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentyl ester

Butyric acid (R)-2-butyryloxymethyl-4-(2,4-difluoro-phenyl)-4-hydroxy-5-[1,2,4]triazol-1-yl-pentyl ester

Acetic acid (R)-2-acetoxymethyl-4-(2,4-difluoro-phenyl)-4-hydroxy-5-[1,2,4]triazol-1-yl-pentyl ester

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