95058-92-7

Basic information

• Product Name: Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate
• Synonyms: 3-(2,2-Dimethyl[1,3]dioxolan-4-yl)-2,2-difluora-3-hydroxy-propionic acid ethyl ester;ethyl (3r,s)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate;Ethyl(3RS)-2,2-Difluoro-3-(2,2-Dimethylioxolan-4-yl)Propionate;D-ERYTHRO-PENTONIC ACID, 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-, ETHYL ESTER;2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-D-ERYTHROPENTONIC ACID ETHYL ESTER;Ethyl(3RS)-2,2-Difluoro-3-(2,2-dimethyldioxolan-4-yl)propionate;propionate (T3);D-erythro-Pentonic acid, 2-deoxy-2,2-difluoro-4,5-O-(1-methylethylidene)-, ethyl ester (9CI)
• CAS NO: 95058-92-7
• Molecular Formula: C₁₀H₁₆F₂O₅
• Molecular Weight: 254.23
• EINECS: 1312995-182-4
• Product Categories: INTERMEDIATESOFGEMCITABINE;API intermediates;Chiral Reagents. Pharmaceuticals;Intermediates & Fine Chemicals
• Mol File: 95058-92-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 338.388 °C at 760 mmHg
• Flash Point: 158.451 °C
• Appearance: /
• Density: 1.232 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.428
• Solubility: Chloroform, Dichloromethane, Methanol
• PKA: 11.95±0.20(Predicted)
• CAS DataBase Reference: Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate(95058-92-7)
• EPA Substance Registry System: Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate(95058-92-7)

Safety Data

• Hazardous Substances Data: 95058-92-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16F2O5/c1-4-15-8(14)10(11,12)7(13)6-5-16-9(2,3)17-6/h6-7,13H,4-5H2,1-3H3/t6-,7-/m1/s1

Upstream product

• 383-62-0 ethyl 2-chloro-2,2-difluoroacetate 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 667-27-6 Ethyl bromodifluoroacetate 
• 53735-98-1 (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol 
• 928797-50-6 ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate 
• 942296-13-1 ethyl (D-erythro)-3-(4-chlorophenylcarbamoyloxy)-2,2-difluoro-3-(2,2-dimethyl-dioxalane-4-yl)propionate 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 

Downstream Products

• 1147119-08-1 C₇H₁₂F₂O₅ 
• 95058-77-8 2-deoxy-2,2-difluoro-1-carbonylribose 
• 1147119-10-5 (3R,4R)-2,2-Difluoro-3,4,5-trihydroxy-pentanoic acid 
• 122111-03-9 gemcitabine hydrochloride 
• 1147119-07-0 (3R,4R)-5-trityloxy-3-hydroxy-2,2-difluoro-pentanoic acid γ-lactone 
• 1147119-11-6 (3R,4R)-5-trityloxy-3-benzoyloxy-2,2-difluoro-pentanoic acid γ-lactone 
• 1147119-15-0 (2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(trityloxymethyl)tetrahydrofuran-3-yl Benzoate 
• 1147119-14-9 (2R,3R)-4,4-difluoro-5-iodo-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate 
• 1147119-13-8 (2R,3R)-4,4-difluoro-5-(methylsulfonyloxy)-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate 
• 143234-90-6 Benzoic acid (R)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-ethoxycarbonyl-2,2-difluoro-ethyl ester 
• 122111-07-3 Benzoic acid (2R,3R)-4,4-difluoro-2-hydroxymethyl-5-oxo-tetrahydro-furan-3-yl ester 
• 143234-91-7 Benzoic acid (1R,2R)-1-(ethoxycarbonyl-difluoro-methyl)-2,3-dihydroxy-propyl ester 

Relevant articles and documents

Preparation method of gemcitabine key intermediate

The invention relates to a preparation method of a gemcitabine key intermediate, and belongs to the technical field of drug intermediate synthesis. In order to solve the problems of high reaction condition requirements and high raw material cost in the prior art, the invention provides a preparation method of a gemcitabine key intermediate, which is characterized by comprising the following steps of: adding ethyl difluorochloroacetate, magnesium metal and a silanization reagent into a polar organic solvent for reaction to obtain an intermediate silyl enol ether; and under the action of Lewis acid, carrying out an aldol condensation reaction on the silyl enol ether and a compound R-glyceraldehyde acetonide as shown in a formula Vto obtain a corresponding product, namely, a gemcitabine key intermediate. According to the method, a target product with high chiral purity and yield can be effectively generated, the product yield reaches 85% or above, and the chiral purity of the product reaches 95% or above.

STEREOSELECTIVE SYNTHESIS OF BETA-NUCLEOSIDES

A process of stereoselectively synthesizing β-nucleoside of formula (I), e.g., 2'-deoxy-2,2'-difluorocytidine, is described. The process includes reacting a tetrahydrofuran compound of the following formula: in which wherein R1, R2, R3, R4, and L as defined in the specification, with a nucleobase derivative in the presence of an oxidizing agent.

PROCESS FOR PREPARING OF 2'-DEOXY-2'2'-DIFLUOROCYTIDINE

Disclosed is a method for preparing 2'-deoxy-2',2'-difluorocytidine of Formula I comprising, preparing an optically pure 3R-hydroxypropane amide compound of Formula VIII from an optical ester compound of Formula IX using an optically active chiral amine,