Diastereospecific chemical synthesis of ribonucleosides-3',4',5',5'-D4

Anna Trifonova, András Földesi, Z. Dinya, Jyoti Chattopadhyaya

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The diastereospecific chemical syntheses of uridine-3',4',5',5'-d4, cytidine-3',4',5',5'-d4, adenosine-3',4',5',5'-d4 and guanosine- 3',4',5',5'-d4 (>97 atom % 2H at C3', C4' and C5') have been achieved by condensation of appropriately protected aglycone with 1-O-acetyl 2,3,5-tri- O-(4-toluoyl)-α/β-D-ribofuranose-3,4,5,5'-d4 (27), which has been obtained in an overall yield of 20 % in 11 steps starting from 50 mmol of 2:5,6-Di-O- isopropylidene-α-D-glucose.

Original languageEnglish
Pages (from-to)4747-4762
Number of pages16
JournalTetrahedron
Volume55
Issue number15
DOIs
Publication statusPublished - Apr 9 1999

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Ribonucleosides
Cytidine
Guanosine
Uridine
Adenosine
Condensation
Glucose
Atoms
propylene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Diastereospecific chemical synthesis of ribonucleosides-3',4',5',5'-D4. / Trifonova, Anna; Földesi, András; Dinya, Z.; Chattopadhyaya, Jyoti.

In: Tetrahedron, Vol. 55, No. 15, 09.04.1999, p. 4747-4762.

Research output: Contribution to journalArticle

Trifonova, Anna ; Földesi, András ; Dinya, Z. ; Chattopadhyaya, Jyoti. / Diastereospecific chemical synthesis of ribonucleosides-3',4',5',5'-D4. In: Tetrahedron. 1999 ; Vol. 55, No. 15. pp. 4747-4762.
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