957-77-7

Basic information

• Product Name: 5-HYDROXYURIDINE
• Synonyms: 5-HYDROXYURIDINE;1-(β-D-Ribofuranosyl)-5-hydroxypyrimidine-2,4(1H,3H)-dione;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-pyrimidine-2,4-dione;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrimidine-2,4-dione;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-5-hydroxy-pyrimidine-2,4-quinone;Uridine, 5-hydroxy-;1-beta-D-Ribofuranosylisobarbituric acid
• CAS NO: 957-77-7
• Molecular Formula: C₉H₁₂N₂O₇
• Molecular Weight: 260.2
• EINECS: 213-487-1
• Mol File: 957-77-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.848g/cm³
• Refractive Index: 1.698
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Water (Slightly, Heated, Sonicated)
• CAS DataBase Reference: 5-HYDROXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXYURIDINE(957-77-7)
• EPA Substance Registry System: 5-HYDROXYURIDINE(957-77-7)

Safety Data

• Hazardous Substances Data: 957-77-7(Hazardous Substances Data)

Usage

Uses

5-Hydroxyuridine is a uridine (U829910), a nucleoside; widely distributed in nature. Uridine is one of the four basic components of ribonucleic acid (RNA).

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 articles and documents

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.