143157-24-8

Basic information

• Product Name: 1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate
• Synonyms: 1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate;1-(3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl)-2,4(1H,3H)-pyriMidinedione
• CAS NO: 143157-24-8
• Molecular Formula: C₂₃H₁₈F₂N₂O₇
• Molecular Weight: 472.3950264
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Impurities;Nucleotides;Carbohydrates & Derivatives, Heterocycles, Impurities, Nucleotides, Bases & Related Reagents
• Mol File: 143157-24-8.mol

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Methanol
• CAS DataBase Reference: 1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate(143157-24-8)
• EPA Substance Registry System: 1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate(143157-24-8)

Safety Data

• Hazardous Substances Data: 143157-24-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Protected epimer of a Gemcitabine degradation product.

Upstream product

• 134877-42-2 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 
• 890044-84-5 (2R,3R)-5-acetoxy-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate 

Relevant articles and documents

A linear synthesis of gemcitabine

Gemcitabine, 2′-deoxy-2′,2′-difluorocytidine, is currently prescribed against a number of cancers. Here we report a linear synthesis of gemcitabine with a high-yielding direct conversion of 3,5-di-O-benzoyl-2-deoxy-2,2-difluororibose into the corresponding glycosyl urea as the key step, followed by conventional conversion to the cytosine base via the uracil derivative. The process proceeded with modest anomeric selectivity.

DIFLUORONUCLEOSIDES AND PROCESS FOR PREPARATION THEREOF

A stereoselective process for the preparation of a 2’,2’-difluronucleoside is provided. In the process, a protected 2’,2’-difluorofuranose is coupled with a base selected from the group consisting of pyrimidine and purine derivatives in the presence of a Lewis acid, wherein the protected 2’,2’-difluorofuranose has a 1-position leaving group and 3- and 5-position protecting groups, and, when the base comprises 1 or more oxygen atoms, the base is a protected base, wherein each oxygen atom is protected with a protecting group.

Stereospecific synthesis of 2-deoxy-2,2-difluororibonolactone and its use in the preparation of 2'-deoxy-2',2'-difluoro-β-D-ribofuranosyl pyrimidine nucleosides: The key role of selective crystallization

A stereospecific synthesis of 2'-deoxy-2',2'-difluorocytidine (gemcitabine), a potential anticancer agent, is described. The stereoselectivity was accomplished via two diastereoselective crystallizations, i.e. the crystallization of the key intermediate, difluororibonolactone 2a, and the crystallization of the hydrochloride salt of gemcitabine 16b from the anomeric mixture. Because of the availability of 2a in large quantities, other 2'-deoxy-2',2'-difluoropyrimidine nucleosides such as 2'-deoxy-2',2'-difluorouridine (19) were synthesized for structure-activity relationship studies.