95058-85-8

Basic information

• Product Name: α-Gemcitabine
• Synonyms: 2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2,2-difluoro-Alpha-D-erythro-pentofuranosyl)-
• CAS NO: 95058-85-8
• Molecular Formula: C₉H₁₁F₂N₃O₄
• Molecular Weight: 263.200846
• Mol File: 95058-85-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: α-Gemcitabine(CAS DataBase Reference)
• NIST Chemistry Reference: α-Gemcitabine(95058-85-8)
• EPA Substance Registry System: α-Gemcitabine(95058-85-8)

Safety Data

• Hazardous Substances Data: 95058-85-8(Hazardous Substances Data)

Usage

General Description

α-Gemcitabine is a modified form of the chemotherapy drug gemcitabine, designed to improve its effectiveness in treating cancer. It is a nucleoside analogue that inhibits the synthesis of DNA, leading to the death of rapidly dividing cancer cells. α-Gemcitabine has been shown to have greater stability and reduced side effects compared to gemcitabine, making it a promising option for cancer treatment. It is currently being researched and developed for clinical use in the treatment of various types of cancer, including pancreatic, breast, and lung cancer. Overall, α-Gemcitabine holds potential as a more effective and tolerable chemotherapy option for cancer patients.

Upstream product

• 122111-03-9 gemcitabine hydrochloride 
• 18027-23-1 bis(trimethylsilyl)-N-acetylcytosine 
• 103882-89-9 3,5-bis-O-(tert-butyldimethylsilyl)-1-O-(methanesulfonyl)-2-deoxy-2,2-difluororibose 
• 952408-92-3 1-[2'-deoxy-2',2'-difluoro-3',5'-bis(tert-butyldiphenylsilyloxy)-ribofuranosyl]-cytosine 
• 861445-90-1 C₁₃H₁₅F₂N₃O₆ 
• 1155863-81-2 C₂₃H₁₉F₂N₃O₆ 
• 1173700-36-1 1-methylsulfonyl-2-deoxy-2,2-difluoro-3,5-di-O-(triisopropylsilyl)-D-ribofuranose 
• 1260238-57-0 2'-deoxy-2',2'-difluoro-3',5'-di-O-(triisopropylsilyl)cytidine 
• 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 

Relevant articles and documents

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.

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.

PREPARATION OF GEMCITABINE

A process for preparation of gemcitabine hydrochloride and purification thereof.