134877-43-3

Basic information

• Product Name: 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose
• Synonyms: 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose;3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose(β-form);(3S,4R)-3-Benzoyl-2,2-difluoro-3,4,5-trihydroxy-6-oxo-6-phenylhexanoic Methanesulfonic anhydride;((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzo;3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-ribofuranose;((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl be;Gemcitabine Impurity 4;β-D-erythro-Pentofuranose
• CAS NO: 134877-43-3
• Molecular Formula: C₂₀H₁₈F₂O₈S
• Molecular Weight: 456.4139264
• EINECS: 1312995-182-4
• Mol File: 134877-43-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 588.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• Refractive Index: 1.555
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose(134877-43-3)
• EPA Substance Registry System: 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose(134877-43-3)

Safety Data

• Hazardous Substances Data: 134877-43-3(Hazardous Substances Data)

Usage

Description

3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose, also known as 2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate β-D-erythro-Pentofuranose, is a chemical compound derived from the modification of ribose, a sugar molecule. It is characterized by the presence of two benzoyl groups at the 3 and 5 positions, a methanesulfonyloxy group at the 1 position, and a difluoro group at the 2 position. 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose is known for its potential applications in the pharmaceutical industry, particularly as an impurity in the synthesis of anticancer agents.

Uses

Used in Pharmaceutical Industry:
3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose is used as an impurity in the synthesis of Gemcitabine (G305028), a potential anticancer agent. Its presence in the synthesis process is crucial for the development of effective cancer treatments, as it may contribute to the overall activity and efficacy of the final drug product.
As an impurity in Gemcitabine synthesis:
3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose is used as a synthetic intermediate for the production of Gemcitabine, an anticancer drug. Its role in the synthesis process is essential for the development of this drug, which has shown promise in treating various types of cancer, including pancreatic, non-small cell lung, and bladder cancers. The compound's presence in the synthesis may enhance the drug's effectiveness and contribute to its overall therapeutic potential.

InChI:InChI=1/C20H18F2O9S/c1-32(27,28)31-19(26)20(21,22)16(30-18(25)14-10-6-3-7-11-14)15(23)12-29-17(24)13-8-4-2-5-9-13/h2-11,15-16,23H,12H2,1H3/t15-,16-/m1/s1

Upstream product

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

Downstream Products

• 134790-40-2 C₂₃H₁₉F₂N₃O₆ 
• 134790-39-9 (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate 
• 103882-84-4 2’-deoxy-2’,2’-difluoro-cytidine 
• 143157-24-8 uridine 
• 143157-27-1 ((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate 
• 155568-06-2 3',5'-di-O-benzoyl-2'deoxy-2',2',5-trifluorocytidine 
• 1203469-67-3 C₂₇H₂₃F₂N₃O₇ 
• 183202-53-1 3-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-ribofuranosyl)-7-acetyl-3,5,6,7-tetrahydro-2H-pyrrolo[2,3-d]pyrimidin-2-one 
• 1006598-32-8 1-(3',5'-di-O-benzoyl-2',2'-difluoro-α-D-pentofuranos-1'-yl)-5-(E)-bromovinyluracil 
• 1006598-31-7 1-(3',5'-di-O-benzoyl-2',2'-difluoro-β-D-pentofuranos-1'-yl)-5-(E)-bromovinyluracil 
• 1251462-76-6 1-(3,3-difluoro-4-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-1,3,4,7-tetrahydro-[1,3]diazepin-2-one 
• 1251462-79-9 1-(3,3-difluoro-4-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-1,3,4,7-tetrahydro-[1,3]diazepin-2-one 
• 1397372-10-9 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 156124-78-6 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Method for recovering mother liquor of gemcitabine intermediate

The invention provides a method for recovering mother liquor of a gemcitabine intermediate, and relates to the technical field of purification. The method for recovering the mother liquor of the gemcitabine intermediate provided by the invention comprises the following steps of: performing acidolysis of crystallization mother liquor containing a compound 5 and a compound 10 so as to obtain a mixture of a compound 3 and a compound 9; mixing the mixture of the compound 3 and the compound 9 with aniline, and performing dehydration reaction to obtain a mixture of Schiff base 12 and the compound 9; performing separation of the mixture of the Schiff base 12 and the compound 9 to obtain high-purity Schiff base 12; performing hydrolysis of the high-purity Schiff base 12 to obtain the compound 3; and mixing the compound 3 with methylsulfonyl chloride, and performing acylation reaction so as to obtain the high-purity compound 5. The method provided by the invention can remove the compound 10 in the crystallization mother liquor to obtain the high-purity compound 5, so that the yield and the purity of hydrochloride, namely gemcitabine hydrochloride, are improved.

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.