149809-43-8

Basic information

• Product Name: (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester
• Synonyms: Posaconazole InterMediates;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-(1H-1,2,4-triazol-1-yl)Methyltetrahydrofuran-3-ylMethyl ester- (POA);(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4;Toluene-4-sulfonica cid 5-(2,4-difluoro-phenyl)-5-[1,2,4]triazol-1-ylMethyl-tetrahydro-furan-3-ylMethyl ester;Posaconazole InterMediate;Posaconazole inter-1;(5R-cis)-Toluene-4-sulfonic acid
• CAS NO: 149809-43-8
• Molecular Formula: C₂₁H₂₁F₂N₃O₄S
• Molecular Weight: 449.47
• EINECS: 1308068-626-2
• Product Categories: Pharmaceuticals;Aromatics;Chiral Reagents;Intermediates;Intermediates & Fine Chemicals
• Mol File: 149809-43-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 100-102°C
• Boiling Point: 608.1 °C at 760 mmHg
• Flash Point: 321.6 °C
• Appearance: /
• Density: 1.40
• Vapor Pressure: 9.85E-15mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: slightly sol. in Chloroform
• PKA: 2.75±0.10(Predicted)
• CAS DataBase Reference: (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester(149809-43-8)
• EPA Substance Registry System: (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester(149809-43-8)

Safety Data

• Hazardous Substances Data: 149809-43-8(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 149809-43-8 differently. You can refer to the following data:
1. Posaconazole intermediate. Antifungal agent.
2. Posaconazole intermediate. Antifungal agent

InChI:InChI=1/C21H21F2N3O4S/c1-15-2-5-18(6-3-15)31(27,28)30-11-16-9-21(29-10-16,12-26-14-24-13-25-26)19-7-4-17(22)8-20(19)23/h2-8,13-14,16H,9-12H2,1H3/t16-,21-/m0/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 156570-15-9 1-(2-(2,4-difluorophenyl)allyl)-1H-1,2,4-triazole 
• 159276-58-1 1-(1-Bromomethyl-vinyl)-2,4-difluoro-benzene 
• 149809-38-1 (R)-4-(2,4-Difluoro-phenyl)-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentane-1,4-diol 
• 110931-77-6 4-(2,4-difluorophenyl)-4-oxobutanoic acid 
• 165115-70-8 4-(2,4-difluorophenyl)-pent-4-enoic acid 
• 1350466-82-8 C₁₄H₁₅F₂N₃O₂*ClH 
• 159276-62-7 diethyl 2-[2-(2,4-difluorophenyl)-2-propen-1-yl]-1,3-propanedioate 
• 156570-10-4 1-(1-chloromethylethenyl)-2,4-difluorobenzene 

Downstream Products

• 184378-04-9 C₃₀H₃₂F₂N₆O₂ 
• 171228-49-2 posaconazote 
• 1350560-57-4 C₃₇H₄₄F₂N₈O₅ 
• 1370190-85-4 (R)-1-((2-(2,4-difluorophenyl)-4-methylenetetrahydrofuran-2-yl)methyl)-1H-1,2,4-triazole 
• 1931946-73-4 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 
• 170985-86-1 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 
• 310882-29-2 6-[(3S,5R)-5-(2,4-Difluoro-phenyl)-5-[1,2,4]triazol-1-ylmethyl-tetrahydro-furan-3-yl]-2-methyl-hexan-3-one oxime 
• 310882-15-6 (2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 
• 310882-25-8 (2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxo-2-hexenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 
• 310882-12-3 (2R-cis)-2-(2,4-difluorophenyl)-4-formylmethyl-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 
• 310882-09-8 (2R-cis)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 

Relevant articles and documents

Preparation method of posaconazole intermediate

The invention relates to the technical field of medicine preparation, and especially relates to a preparation method of a posaconazole intermediate. The preparation method comprises the following steps: reacting a compound as shown in a formula II, serving as a raw material, with 1, 2, 4-triazole to obtain a compound as shown in a formula III, and then reacting with air or oxygen under the action of a catalyst 1 to obtain a compound as shown in a formula IV; reacting the compound as shown in the formula IV with dimethyl malonate to obtain a compound as shown in a formula V; reacting the compound shown in the formula V under the action of a reducing agent to obtain a compound shown in a formula VI; and finally, carrying out intramolecular etherification reaction on the compound shown in the formula VI, and carrying out sulfonylation reaction on the obtained product to obtain a target product I. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, few reaction steps, high yield and high purity of the obtained product.

Preparation method for preparing posaconazole midbody

The invention provides a method for preparing a posaconazole midbody shown as the formula 1. According to the preparation method, a compound 2 reported in literature is used as a raw material; firstly, trialkyl silane is used for protecting hydroxyl to obtain a compound 3; then, the compound 3 takes a reaction with sodium salts 4 of triazole to obtain a compound 5; next, siloxane removal is performed under the effects of paratoluensulfonyl chloride and alkali, and toluenesulfonyl protection is performed to obtain a compound 1. The method provided by the invention can overcome the defects in the prior art; a splicing step is not performed; the occurrence of side reaction and the appearance of impurities are reduced; the reaction selectivity and the yield are improved. The formulas are shown as the accompanying drawing.

Process for the Preparation of Triazole Antifungal Drug, Its Intermediates and Polymorphs Thereof

A process for the preparation of 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy]phenyl]-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one compound of formula-1, its intermediates and polymorphs thereof. (I)