166376-97-2

Basic information

• Product Name: 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-ERYTHRO-PENTONIC ACID, ETHYL ESTER
• Synonyms: 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-ERYTHRO-PENTONIC ACID, ETHYL ESTER
• CAS NO: 166376-97-2
• Molecular Formula: C10H16F2O5
• Molecular Weight: 254.227
• Mol File: 166376-97-2.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 338.388°C at 760 mmHg
• Flash Point: 158.451°C
• Appearance: /
• Density: 1.232g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.428
• CAS DataBase Reference: 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-ERYTHRO-PENTONIC ACID, ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-ERYTHRO-PENTONIC ACID, ETHYL ESTER(166376-97-2)
• EPA Substance Registry System: 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-ERYTHRO-PENTONIC ACID, ETHYL ESTER(166376-97-2)

Safety Data

• Hazardous Substances Data: 166376-97-2(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-/m0/s1

Upstream product

• 667-27-6 Ethyl bromodifluoroacetate 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 860649-42-9 5,6-0-isopropylidene ascorbic acid 
• 5736-03-8 (d,l) isopropylidene glyceraldehyde 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 928797-50-6 ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate 
• 92973-39-2 O³,O⁴-(1-methylethylidene)-L-threonic acid 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 109522-62-5 (2-ethoxy-1,1-difluoro-2-oxoethyl)zinc(II) bromide 
• 383-62-0 ethyl 2-chloro-2,2-difluoroacetate 
• 53735-98-1 (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol 
• 942296-13-1 ethyl (D-erythro)-3-(4-chlorophenylcarbamoyloxy)-2,2-difluoro-3-(2,2-dimethyl-dioxalane-4-yl)propionate 
• 136136-17-9 O³,O⁴-(1-methylethylidene)-D-erythronic acid 
• 50271-42-6 5,6-O-isopropylidene-D-isoascorbic acid 

Downstream Products

• 95058-92-7 (erytro) ethyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy propionate 
• 122111-01-7 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate 
• 1173824-58-2 (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate 
• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 
• 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 
• 211807-33-9 (R)-3,3-Difluoro-5-hydroxymethyl-dihydro-furan-2-one 
• 166275-26-9 (4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,3-difluoro-dihydro-furan-2-one 
• 166275-25-8 (4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one 

Relevant articles and documents

Deoxyribonolactone lesion in DNA: Synthesis of fluorinated analogues

Mono- and difluorinated derivatives of 2-deoxyribonolactone were synthesized using diastereoselective Reformatski reaction as a key step.

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.

Preparation method of intermediate of antitumor drug gemcitabine hydrochloride

The invention relates to a preparation method of a intermediate of antitumor drug gemcitabine hydrochloride. According to the method, D-isoascorbic acid is used as a starting raw material and reacts with 2,2-dimethylpropane under the catalysis of p-toluenesulfonic acid in the presence of acetone serving as a solvent to protect hydroxyl groups at 5 and 6 sites to obtain T1; then, hydrogen peroxideis used for carrying out oxidation under the alkaline condition to obtain T2; the T2 is oxidized by sodium hypochlorite to obtain T3; the T3 and ethyl bromodifluoroacetate are subjected to a Reformatsky reaction to obtain T4; then the T4 is subjected to deprotection and cyclization under the catalysis of trifluoroacetic acid to obtain T5; the T5 and benzoyl chloride are subjected to an esterification reaction under the catalysis of DMAP to obtain T6, and a synthetic route II is shown in the specification.