957-77-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxyuridine is used as a pharmaceutical agent for its potential therapeutic effects. It has been found to exhibit antiviral, anticancer, and immunomodulatory properties, making it a valuable compound for the development of new drugs and therapies.
Used in Research Applications:
5-Hydroxyuridine is used as a research tool in molecular biology and biochemistry. It is employed in various experimental procedures, such as studying the mechanisms of RNA synthesis, regulation, and function, as well as investigating the role of modified nucleosides in RNA stability and gene expression.
Used in Drug Development:
5-Hydroxyuridine is used in drug development for its potential as a lead compound in the synthesis of novel therapeutic agents. Its unique chemical structure allows for the design and development of new drugs with improved efficacy, selectivity, and reduced side effects.
Used in Diagnostic Applications:
5-Hydroxyuridine is used in diagnostic applications for its ability to serve as a biomarker for certain diseases and conditions. Its presence in biological samples can provide valuable information about the progression of diseases and the effectiveness of treatments.
Used in Cosmetic Industry:
5-Hydroxyuridine is used in the cosmetic industry for its potential skin health benefits. It has been found to possess antioxidant and anti-inflammatory properties, which can contribute to improved skin hydration, elasticity, and overall health.

InChI:InChI=1/C9H12N2O7/c12-2-4-5(14)6(15)8(18-4)11-1-3(13)7(16)10-9(11)17/h1,4-6,8,12-15H,2H2,(H,10,16,17)/t4-,5-,6-,8-/m1/s1

Synthetic route

5-bromouridine (957-75-5) → 5',6-anhydro-6-hydroxyuridine (15425-10-2) + 1-(β-D-ribofuranosyl)-2-oxo-4-imidazoline-4-carboxylic acid (19556-57-1) + 5-Hydroxy-uridin (957-77-7) + 6-hydroxyuridine (123131-51-1)

Conditions	Yield
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration;

5-Hydroxy-uridin (957-77-7) + 2-(triphenylphosphoranylidene)acetamide (38821-11-3) → 5-(carbamoylmethyl)uridine (29569-30-0)

Conditions	Yield
In 1,4-dioxane Heating;	99%

Acetyl bromide (506-96-7) + 5-Hydroxy-uridin (957-77-7) → 1-(2-bromo-2-deoxy-3,5-di-O-acetylribosyl)-5-acetoxyuracil (151412-49-6) + Acetic acid (2R,3R,4S,5R)-5-(5-acetoxy-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-acetoxymethyl-4-bromo-tetrahydro-furan-3-yl ester

Conditions	Yield
In acetonitrile at 60℃;	A 95% B 5%

5-Hydroxy-uridin (957-77-7) + 2,2-dimethoxy-propane (77-76-9) → 2',3'-O-isopropylidene-5-hydroxyuridine (20406-82-0)

Conditions	Yield
With toluene-4-sulfonic acid for 48h; Ambient temperature;	84%

Acetyl bromide (506-96-7) + 5-Hydroxy-uridin (957-77-7) → 1-(2-bromo-2-deoxy-3,5-di-O-acetylribosyl)-5-acetoxyuracil (151412-49-6) + Acetic acid (2R,3R,4S,5R)-5-(5-acetoxy-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-acetoxymethyl-4-bromo-tetrahydro-furan-3-yl ester + O3',O5'-diacetyl-5,2'-dibromo-2'-deoxy-uridine (57777-91-0)

Conditions	Yield
With hydrogen bromide; acetic acid In acetonitrile at 60℃;	A 76% B 5% C 16%

5-Hydroxy-uridin (957-77-7) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → 5-<(methylcarboxy)methyl>uridine (29428-50-0)

Conditions	Yield
In 1,4-dioxane Heating;	67%

5-Hydroxy-uridin (957-77-7) + chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → 5'-O-(silyl)-5-(siloxy)uridine (151412-61-2)

Conditions	Yield
With pyridine for 50h; Ambient temperature;	65%

5-Hydroxy-uridin (957-77-7) → 4-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3,4-dihydro-[1,2,3]triazolo[4,5-d]pyrimidine-5,7-dione

Conditions	Yield
With sodium azide In tetrahydrofuran at 80℃; for 5h;	62%

5-Hydroxy-uridin (957-77-7) + 2-amino-benzenethiol (137-07-5) → 1,5-dihydro-1-β-D-ribosyl-2H-pyrimido[4,5-b][1,4]benzothiadine-2,4(3H)-dione

Conditions	Yield
Stage #1: 5-Hydroxy-uridin With N-Bromosuccinimide In ethanol at 20℃; for 0.5h; Stage #2: 2-amino-benzenethiol In ethanol for 1h; Heating;	59%

5-Hydroxy-uridin (957-77-7) + propargyl bromide (106-96-7) → 5-(2-propynyloxy)-3-N-(2-propynyl)uridine + 5-(2-propynyloxy)uridine (35042-07-0)

Conditions	Yield
With sodium hydroxide In methanol; water at 25℃; for 12h;	A 12% B 57%

Iodoacetic acid (64-69-7) + 5-Hydroxy-uridin (957-77-7) → 3-carboxymethyl-5-hydroxyuridine

Conditions	Yield
With sodium hydroxide In water for 16h; Ambient temperature;	54%

5-Hydroxy-uridin (957-77-7) + 2,2-dimethoxy-propane (77-76-9) + acetone (67-64-1) → 2',3'-O-isopropylidene-5-hydroxyuridine (20406-82-0) + 2',3'-O-isopropylidene-5'-O-(2-methoxy-2-propyl)-5-hydroxyuridine (189069-55-4)

Conditions	Yield
With toluene-4-sulfonic acid for 22h; Ambient temperature;	A 37% B 30%

5-Hydroxy-uridin (957-77-7) + triethylamine carbonate (15715-58-9) → 5-hydroxy-uridine-TP tetrakistriethylammonium salt

Conditions	Yield
Stage #1: 5-Hydroxy-uridin With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere; Stage #3: triethylamine carbonate Further stages;	4.13%

5-Hydroxy-uridin (957-77-7) + triethylamine carbonate (15715-58-9) → 5-hydroxy-UTP tetrakis(triethylammonium) salt

Conditions	Yield
Stage #1: 5-Hydroxy-uridin With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere; Stage #3: triethylamine carbonate Further stages;	4.13%

5-Hydroxy-uridin (957-77-7) + 4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl (14691-88-4) → 5-<(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)amino>uridine

Conditions	Yield
With sulfuric acid In water for 7.5h;	30 mg

5-Hydroxy-uridin (957-77-7) + p-toluidine (106-49-0) → 5-(p-toluidino)uridine

Conditions	Yield
With sulfuric acid In water for 6h;	24 mg

5-Hydroxy-uridin (957-77-7) + aniline (62-53-3) → 5-anilinouridine

Conditions	Yield
With sulfuric acid In water for 6h;	44 mg

5-Hydroxy-uridin (957-77-7) → 1-(β-D-ribofuranosyl)-2-oxo-4-imidazoline-4-carboxylic acid (19556-57-1)

Conditions	Yield
With sodium hydroxide at 90.1℃; Rate constant; decomposition, various reagent concentration;

(tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4) + 5-Hydroxy-uridin (957-77-7) → [1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetic acid tert-butyl ester (189069-50-9)

Conditions	Yield
In 1,4-dioxane for 9h; Heating;	2.59 g

5-Hydroxy-uridin (957-77-7) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate (4336-39-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2.59 g / dioxane / 9 h / Heating 2: 2.55 g / pyridine / 16 h / Ambient temperature 3: 68 percent / TFA / CH2Cl2 / 1 h / Ambient temperature View Scheme

5-Hydroxy-uridin (957-77-7) → 2',3',5'-tri-O-acetyl-5-t-butoxycarbonylmethyluridine (189069-51-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.59 g / dioxane / 9 h / Heating 2: 2.55 g / pyridine / 16 h / Ambient temperature View Scheme

5-Hydroxy-uridin (957-77-7) → 5'-O-(silyl)-2,2'-anhydro-5-(siloxy)uridine

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / pyridine / 50 h / Ambient temperature 2: 63 percent / dimethylformamide / Ambient temperature View Scheme

5-Hydroxy-uridin (957-77-7) → 5'-O-(silyl)-2',3'-dideoxydidehydro-5-<(dimethyl-2-(2,3-dimethylbutyl))silyloxy>uridine

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / pyridine / 50 h / Ambient temperature 2: 12 percent / dimethylformamide / Ambient temperature 3: 73 percent / P(OCH3)3 / 3 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 65 percent / pyridine / 50 h / Ambient temperature 2: 74 percent / 1,2-dichloro-ethane / 4 h / Ambient temperature 3: 73 percent / P(OCH3)3 / 3 h / Heating View Scheme

5-Hydroxy-uridin (957-77-7) → 5'-O-(silyl)-2',3'-O-thiocarbonyl-5-(siloxy)uridine (151412-62-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / pyridine / 50 h / Ambient temperature 2: 12 percent / dimethylformamide / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 65 percent / pyridine / 50 h / Ambient temperature 2: 74 percent / 1,2-dichloro-ethane / 4 h / Ambient temperature View Scheme

5-Hydroxy-uridin (957-77-7) → 2',3'-O-isopropylidene-5-(ethoxycarbonylmethoxy)uridine (110417-93-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / p-TosOH / 48 h / Ambient temperature 2: 48 percent / 1 M NaOH / aq. ethanol / 3 h / Ambient temperature View Scheme

5-Hydroxy-uridin (957-77-7) → 2',3'-O-isopropylidene-2,5'-anhydro-5-(ethoxycarbonylmethoxy)uridine (112145-74-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / p-TosOH / 48 h / Ambient temperature 2: 48 percent / 1 M NaOH / aq. ethanol / 3 h / Ambient temperature 3: 90 percent / (C6H5)3P, (C2H5)3N, ethyl azadicarboxylate / dioxane / 3 h View Scheme

5-Hydroxy-uridin (957-77-7) → 2',3'-O-isopropylidene-5-ethoxycarbonylmethoxy-2-thiouridine (112145-76-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / p-TosOH / 48 h / Ambient temperature 2: 48 percent / 1 M NaOH / aq. ethanol / 3 h / Ambient temperature 3: 90 percent / (C6H5)3P, (C2H5)3N, ethyl azadicarboxylate / dioxane / 3 h 4: 32 percent / H2S / pyridine / 120 h / Ambient temperature View Scheme

5-Hydroxy-uridin (957-77-7) → uridine 5-oxyacetic acid methyl ester (66536-81-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / p-TosOH / 48 h / Ambient temperature 2: 48 percent / 1 M NaOH / aq. ethanol / 3 h / Ambient temperature 3: 83 percent / 1 M HCl / 48 h / Ambient temperature View Scheme

Upstream product

• 957-75-5 5-bromouridine 

Downstream Products

• 29428-50-0 5-<(methylcarboxy)methyl>uridine 
• 20406-82-0 2',3'-O-isopropylidene-5-hydroxyuridine 
• 29569-30-0 5-(carbamoylmethyl)uridine 
• 4336-39-4 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate 
• 189069-55-4 2',3'-O-isopropylidene-5'-O-(2-methoxy-2-propyl)-5-hydroxyuridine 

Relevant academic research and scientific papers

SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS

This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.

Reactions of 5-bromo substituted pyrimidine nucleosides with aqueous alkalies: kinetics and mechanisms.

Kinetics for the parallel and consecutive steps of the reactions of 5-bromocytidine, 5-bromouridine and its 5'-O-methyl and 2',3'-O-isopropylidene derivatives with aqueous alkalies were studied by LC. The mechanisms of the partial reactions involved are discussed.