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

• 124-63-0 methanesulfonyl chloride 
• 1173824-58-2 (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate 
• 153012-08-9 C₁₉H₁₆F₂O₆ 
• 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

• 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 
• 155131-43-4 1-bromo-2-deoxy-2,2-difluoro-α-D-ribofuranosyl-3,5-dibenzoate 

Relevant articles and documents

High-selectivity synthesis method for gemcitabine intermediate

The invention discloses a high-selectivity synthesis method for a gemcitabine intermediate. The high-selectivity synthesis method specifically comprises the following process: Step 1, synthesis of T1;Step2, synthesis of T2, to be specific, 550kg of hydrogen peroxide is dropwise added into the T1, and a reaction is controlled to produce the T2; Step3, synthesis of T3, to be specific, sodium acetate trihydrate or sodium carbonate is added into a reaction kettle, the PH value is adjusted with glacial acetic acid, a 10%-15% sodium hypochlorite aqueous solution is dropwise added, and a reaction iscontrolled to produce the T3; Step 4, synthesis of T4; Step 5, synthesis of T5; Step 6, synthesis of T6; Step 7, synthesis of T7; Step 8, synthesis of T8; and Step9, T8 configuration transformation.The high-selectivity synthetic method for the gemcitabine intermediate can reduce the production cost, and meanwhile, can also increase the yield of the gemcitabine intermediate.

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.