122111-11-9

Basic information

• Product Name: 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate
• Synonyms: D-ERYTHRO-PENTOFURANOSE, 2-DEOXY-2,2-DIFLUORO-, 3,5-DIBENZOATE 1-METHANESULFONATE;2-deoxy-2,2-difluoro-d-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate;2-DEXY-2,2-DIFLUORO-3,5-O-DIBENZOYLRIBOSE MESYLATE;2-Deoxy-2,2-difluoro-D-erythro-ribofuranose-3,5-dibenzoate 1-Methanesulfonate;3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-ribofuranoside;GeMcitabine InterMediate 8;T8, 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-Methanesulfonate;((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-((Methylsulfonyl)oxy)tetrahydrofuran-2-yl)Methyl benzoate
• CAS NO: 122111-11-9
• Molecular Formula: C₂₀H₁₈F₂O₈S
• Molecular Weight: 456.41
• EINECS: 1592732-453-0
• Product Categories: Aromatics Compounds;Aromatics;Carbohydrates & Derivatives;Intermediates
• Mol File: 122111-11-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 588.439 °C at 760 mmHg
• Flash Point: 309.677 °C
• Appearance: Brown liquid
• Density: 1.464 g/cm³
• Vapor Pressure: 2.41E-11mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate(122111-11-9)
• EPA Substance Registry System: 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate(122111-11-9)

Safety Data

• Hazardous Substances Data: 122111-11-9(Hazardous Substances Data)

Usage

Chemical Properties

Brown Liquid

Uses

Different sources of media describe the Uses of 122111-11-9 differently. You can refer to the following data:
1. Gemcitabine intermediate
2. Gemcitabine intermediate.

InChI:InChI=1/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m0/s1

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 1173824-58-2 (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate 
• 122111-01-7 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate 
• 928797-50-6 ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate 
• 95058-77-8 2-deoxy-2,2-difluoro-1-carbonylribose 
• 153012-08-9 C₁₉H₁₆F₂O₆ 

Downstream Products

• 143157-23-7 1-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)-4-acetamidopyrimidin-2-one 
• 134877-42-2 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate 
• 134790-39-9 (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate 
• 95058-81-4 gemcitabine 
• 122111-03-9 gemcitabine hydrochloride 
• 1445381-44-1 (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate 
• 1440537-02-9 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythropentofuranosyl]-5-iodopyrrolo[2,3-d]pyrimidine 
• 1537910-71-6 3',5'-dibenzoyl-2',2'-difluoro-5-aza-α-2'-deoxycytidine 
• 1537910-70-5 3’,5’-dibenzoyl-2’,2’-difluoro-5-aza-deoxycytidine 
• 1440537-03-0 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-5-iodopyrrolo[2,3-d]pyrimidine 
• 1440537-19-8 4-amino-7-[2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-5-phenylpyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Purification method of gemcitabine intermediate

The invention provides a purification method of a gemcitabine intermediate, and belongs to the technical field of drug intermediate synthesis. According to the invention, a compound 2 in an existing method (shown in a formula 1 and a formula 2 in a background art) is reduced to obtain a mixture containing a compound 3 and a byproduct compound 9; the mixture reacts with aniline; dehydration condensation reaction of the compound 3 and aniline is achieved; Schiff base is generated; the Schiff base and the byproduct compound 9 are easy to separate; a high-purity compound 3 can be obtained by performing simple acidic hydrolysis and separation on the separated Schiff base; the high-purity compound 3 is subjected to sulfonylation reaction to synthesize a gemcitabine hydrochloride key intermediate compound 5, so that the yield and the purity of the compound 5 can be improved, and the preparation yield and the product quality of the raw material medicine gemcitabine hydrochloride are ensured.

Azido nucleosides and nucleotide analogs

Disclosed herein are 4′-azido-substituted nucleosides, nucleotides and analogs thereof, pharmaceutical compositions that include one or more of 4′-azido-substituted nucleosides, nucleotides and analogs thereof, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an infection from a paramyxovirus and/or an orthomyxovirus, with a 4′-azido-substituted nucleoside, a nucleotide and/or an analog thereof. Examples of viral infections include a respiratory syncytial viral (RSV) and influenza infection.

Design, synthesis and biological evaluation of 2′-deoxy-2′, 2′-difluoro-5-halouridine phosphoramidate ProTides

We report the synthesis of a series of novel 2′-deoxy-2′, 2′-difluoro-5-halouridines and their corresponding phosphoramidate ProTides. All compounds were evaluated for antiviral activity and for cellular toxicity. Interestingly, 2′-deoxy-2′,2′-difluoro-5-iodo- and -5-bromo-uridines showed selective activity against feline herpes virus replication in cell culture due to a specific recognition (activation) by the virus-encoded thymidine kinase.