ChemicalBook CAS DataBase List 2,2'-Cyclouridine

2,2'-Cyclouridine synthesis

6synthesis methods

Product Name:2,2'-Cyclouridine
CAS Number:3736-77-4
Molecular formula:C9H10N2O5
Molecular Weight:226.19

2,2-Dimethylpropionic acid (2R)-2,3,3aβ,9aβ-tetrahydro-6-oxo-2α-[(pivaloyloxy)methyl]-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3β-yl ester

38642-36-3
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3736-77-4
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Yield:3736-77-4 92%

Reaction Conditions:

with ammonia in methanol at 0 - 20; for 3 h;

Steps:

2,2'-Anhydrouridine (5)
4a (100 mg, 0.25 mmol) was dissolved in 2 mL of MeOH saturated with NH₃. The solution was stirred for 3 hours at 0°C, the solvent was evaporated, and the product was purified on previously washed silica gel column in solvent system D. The column was washed with CH₂Cl₂:MeOH 1:1 v/v. The fractions containing the product were collected and evaporated under diminished pressure. The product was crystallized from DMF and flushed with MeOH resulting in 52.5 mg (0.23 mmol, yield 92%) of 5. The product was 99% pure by RP-HPLC.

References:

Szlenkier, Maurycy;Kamel, Karol;Boryski, Jerzy [Nucleosides, nucleotides and nucleic acids,2016,vol. 35,# 8,p. 410 - 425]

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58-96-8 Synthesis