Broxuridine synthesis
- Product Name:Broxuridine
- CAS Number:59-14-3
- Molecular formula:C9H11BrN2O5
- Molecular Weight:307.1
951-78-0
59-14-3
The general procedure for the synthesis of 5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-diones from 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-diones was carried out under stirring conditions as follows. 2'-O-methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile (H2O:CH3CN = 1:9, 5 mL). Subsequently, NaN3 (0.104 g, 1.6 mmol) was added followed by SMBI (0.101 g, 0.44 mmol) at room temperature. The reaction mixture was continuously stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). The reaction was completed after about 1.5 h. The reaction mixture was filtered, concentrated under reduced pressure and co-evaporated with acetonitrile (2 x 2 mL) to remove residual water. The crude product was purified by column chromatography using a mixture of dichloromethane (DCM) and methanol (MeOH) (4%-6% MeOH in DCM, v/v) as eluent, resulting in purified bromonucleoside 6 (0.117 g, 93% yield) as a white solid.
Yield:59-14-3 25%
Reaction Conditions:
with Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose in aq. buffer at 30; pH=7;Green chemistry;Enzymatic reaction;
Steps:
4.8. Biotransformation of nucleoside analogues
General procedure: Thymidine (dThd) and 2'-deoxyuridine (dUrd) were assayed as sugar donors. Different purine and pyrimidine bases were tested: 5-fluorouracil (5FUra), 5-bromouracil (5BrUra), 5-chlorouracil (5ClUra), 6-chloropurine (6ClPur), 6-bromopurine (6BrPur) and 6-chloro-2-fluoropurine (6Cl2FPur). Reactions were performed using 100 mg/mL of immobilized LaNDT, 6 mM nucleoside and 2 mM base, 30 °C and 200 rpm. At different times (5-8 h), 20 μL aliquots were taken and centrifuged at 10,000 x g, and the supernatant was analyzed by HPLC to evaluate yield expressed as percentage and product conversion expressed as mg of product per gram of support.
References:
Britos, Claudia N.;Lapponi, María José;Cappa, Valeria A.;Rivero, Cintia W.;Trelles, Jorge A. [Journal of Fluorine Chemistry,2016,vol. 186,p. 91 - 96]
951-78-0
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59-14-3
370 suppliers
$7.00/100mg
51-20-7
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$10.00/1g
951-78-0
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$5.00/100mg
59-14-3
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$7.00/100mg
66-22-8
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6161-23-5
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59-14-3
370 suppliers
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