95058-85-8

Usage

Uses

Used in Oncology:
α-Gemcitabine is used as a chemotherapy agent for the treatment of various types of cancer due to its ability to inhibit DNA synthesis in rapidly dividing cancer cells. Its enhanced stability and reduced side effects compared to gemcitabine make it a more tolerable and effective option for cancer patients.
Used in Cancer Research and Development:
α-Gemcitabine is being researched and developed for clinical use in the treatment of different cancer types, including pancreatic, breast, and lung cancer. Its potential as a more effective and tolerable chemotherapy option is currently under investigation, with the aim of improving patient outcomes and quality of life during cancer treatment.

Upstream product

• 18027-23-1 bis(trimethylsilyl)-N-acetylcytosine 
• 103882-89-9 3,5-bis-O-(tert-butyldimethylsilyl)-1-O-(methanesulfonyl)-2-deoxy-2,2-difluororibose 
• 1155863-81-2 C₂₃H₁₉F₂N₃O₆ 
• 1173700-25-8 2-deoxy-2,2-difluoro-3,5-di-O-(triisopropylsilyl)-γ-D-ribonolactone 
• 1173700-23-6 (3S,4R,5R)-3-fluoro-4-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)-dihydrofuran-2(3H)-one 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 1260238-57-0 2'-deoxy-2',2'-difluoro-3',5'-di-O-(triisopropylsilyl)cytidine 
• 1173700-36-1 1-methylsulfonyl-2-deoxy-2,2-difluoro-3,5-di-O-(triisopropylsilyl)-D-ribofuranose 
• 861445-90-1 C₁₃H₁₅F₂N₃O₆ 
• 952408-92-3 1-[2'-deoxy-2',2'-difluoro-3',5'-bis(tert-butyldiphenylsilyloxy)-ribofuranosyl]-cytosine 
• 122111-03-9 gemcitabine hydrochloride 

Relevant academic research and scientific papers

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

HALOGENATED 2-DEOXY-LACTONES, 2'-DEOXY--NUCLEOSIDES, AND DERIVATIVES THEREOF

Disclosed are halogenated 2-deoxy-lactone, 2'-deoxy-nucleosides, and derivatives thereof, for example, a compound of formula (I). Also disclosed are a composition comprising a pharmaceutically acceptable carrier and at least one compound or salt of the invention, and a method of treating a disorder is selected from the group consisting of an abnormal cellular proliferation, a viral infection, and an autoimmune disorder.

Inactivation of lactobacillus leichmannii ribonucleotide reductase by 2',2'-difluoro2'-deoxycytidine s'-triphosphate: Covalent modification

Ribonucleotide reductase (RNR) from Lactobacillus leichmannii, a 76 kDa monomer using adenosylcobalamin (AdoCbl) as a cofactor, catalyzes the conversion of nucleoside triphosphates to deoxynucleotides and is rapidly ( 3H]- and [5-3H]F2CTP were synthesized and used independently to inactivate RNR. Sephadex G-50 chromatography of the inactivation mixture revealed that 0.47 equiv of a sugar was covalently bound to RNR and that 0.71 equiv of cytosine was released. Alternatively, analysis of the inactivated RNR by SDS-PAGE without boiling resulted in 33% of RNR migrating as a 110 kDa protein. Inactivation of RNR with a mixture of [1'-3H]F2CTP and [1'-2H]F 2CTP followed by reduction with NaBH4, alkylation with iodoacetamide, trypsin digestion, and HPLC separation of the resulting peptides allowed isolation and identification by MALDI-TOF mass spectrometry (MS) of a 3H/2H-labeled peptide containing C731 and C736 from the C-terminus of RNR accounting for 10% of the labeled protein. The MS analysis also revealed that the two cysteines were cross-linked to a furanone species derived from the sugar of F2CTP. Incubation of [1-3H]F2CTP with C119S-RNR resulted in 0.3 equiv of sugar being covalently bound to the protein, and incubation with NaBH4 subsequent to inactivation resulted in trapping of 2'-fluoro-2'-deoxycytidine. These studies and the ones in the preceding paper (DOI: 10.1021/bi9021318) allow proposal of a mechanism of inactivation of RNR by F2CTP involving multiple reaction pathways. The proposed mechanisms share many common features with F2CDP inactivation of the class I RNRs.

Efficient syntheses of clofarabine and gemcitabine from 2-deoxyribonolactone

The development of a new methodology to achieve electrophilic fluorination of triisopropylsilyl-protected 2-deoxyribonolactone has been employed to synthesize clofarabine and gemcitabine with improved synthetic efficiency versus prior synthetic methods. These studies highlight the versatility of this new methodology to obtain medically relevant 2′-fluoronucleosides.

AN IMPROVED PROCESS FOR PREPARATION OF GEMCITABINE HYDROCHLORIDE.

A process for isolating ?-anomer enriched Gemcitabine hydrochloride by converting Gemcitabine base into Gemcitabine hydrochloride followed by its purification using solvents from the series of water soluble ethers like 1,4-dioxane or Monoglyme.

Method for the Preparation of 2'-Deoxy-2',2'-Difluorocytidine

This invention relates to an improved method for stereoselectively preparing 2￠￥-deoxy-2￠￥,2￠￥-difluorocytidine of formula (I), which comprises the steps of reacting a 1-halo ribofuranose compound of formula (III) with a nucleobase of formula (IV) in a solvent to obtain a nucleoside of formula (II) with removing the silyl halide of formula (V) produced during the reaction; and deprotecting the nucleoside of formula (II) to obtain 2￠￥-deoxy-2￠￥,2￠￥-difluorocytidine of formula (I).

PREPARATION OF GEMCITABINE

A process for preparation of gemcitabine hydrochloride and purification thereof.

Method for preparation of 2'-deoxy-2', 2'-difluoro-beta-cytidine or pharmaceutically acceptable salts thereof by using 1,6-anhydro-beta-D-glucose as raw material

The present invention provides a method for preparation of 2′-deoxy-2′,2′-difluoro-β-cytidine or pharmaceutically acceptable salt thereof, comprising starting from 1,6-anhydro-β-D-glucose as raw material, oxidizing, and fluorinating to obtain 2-deoxy-2,2-difluoro-D-ribofuranose as intermediate. The 2′-deoxy-2′,2′-difluoro-β-cytidine was finally prepared from the intermediate of 2-deoxy-2,2-difluoro-D-ribofuranose. The method is simple in operation and has a high yield. The method can effectively be used in large-scale production.

METHOD FOR THE PREPARATION OF 2#-DEOXY-2#,2#-DIFLUOROCYTIDINE

This invention relates to an improved method for stereoselectively preparing 2′-deoxy-2′,2′-difluorocytidine of formula (I), which comprises the steps of reacting a 1-halo ribofuranose compound of formula (III) with a nucleobase of formula (IV) in a solvent to obtain a nucleoside of formula (II) with removing the silyl halide of formula (V) produced during the reaction; and deprotecting the nucleoside of formula (II) to obtain 2′-deoxy-2′,2′-difluorocytidine of formula (I).

METHOD FOR THE PREPARATION OF 2'-DEOXY-2',2'-DIFLUOROCYTIDINE

This invention relates to an improved method for stereoselectively preparing 2￠￥-deoxy-2￠￥,2￠￥-difluorocytidine of formula (I), which comprises the steps of reacting a 1-halo ribofuranose compound of formula (III) with a nucleobase of formula (IV) in a solvent to obtain a nucleoside of formula (II) with removing the silyl halide of formula (V) produced during the reaction; and deprotecting the nucleoside of formula (II) to obtain 2￠￥-deoxy-2￠￥,2￠￥-difluorocytidine of formula (I).