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Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine
- Source :
- Tetrahedron. 75:1203-1213
- Publication Year :
- 2019
- Publisher :
- Elsevier BV, 2019.
-
Abstract
- Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.
- Subjects :
- Anomer
Glycosylation
Pyrimidine
010405 organic chemistry
Chemistry
Mesylate
Stereochemistry
Organic Chemistry
010402 general chemistry
01 natural sciences
Biochemistry
Gemcitabine
0104 chemical sciences
carbohydrates (lipids)
chemistry.chemical_compound
N-linked glycosylation
Drug Discovery
medicine
Nucleoside
Cytosine
medicine.drug
Subjects
Details
- ISSN :
- 00404020
- Volume :
- 75
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........0faac22dfc847bb6067c55a4947b1542