Product Name

  • Name

    5-Methyluridine

  • EINECS 215-973-9
  • CAS No. 1463-10-1
  • Article Data71
  • CAS DataBase
  • Density 1.576 g/cm3
  • Solubility
  • Melting Point 183-184 °C(lit.)
  • Formula C10H14N2O6
  • Boiling Point
  • Molecular Weight 258.231
  • Flash Point
  • Transport Information
  • Appearance white powder
  • Safety 24/25
  • Risk Codes 26/27/28
  • Molecular Structure Molecular Structure of 1463-10-1 (5-Methyluridine)
  • Hazard Symbols VeryT+
  • Synonyms 1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;Uridine,5-methyl-;5-Methyl uridine;Thymine riboside;Methyluridine;5-Methyluridin, Ribothymidine;
  • PSA 124.78000
  • LogP -2.54350

Synthetic route

2',3',5'-tri-O-benzoyluridine
3180-76-5

2',3',5'-tri-O-benzoyluridine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With sodium methylate In methanol98%
With ammonia In methanol for 96h;98%
With sodium methylate In methanol for 0.5h; Heating;93%
2',3',5'-tri-O-benzoyluridine
3180-76-5

2',3',5'-tri-O-benzoyluridine

A

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

B

benzamide
55-21-0

benzamide

C

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With ammonia In ethanol at 20℃;A n/a
B n/a
C 95%
1-(5'-O-trityl-β-D-ribofuranosyl)thymine
101796-28-5

1-(5'-O-trityl-β-D-ribofuranosyl)thymine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With carbon tetrabromide In methanol at 20℃; for 12h; Irradiation;94%
With sulfuric acid; water; silica gel In acetonitrile at 25℃; for 0.283333h;93%
1-[5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine
119794-52-4

1-[5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 5.3h;93%
3-Methylthymidin
3650-91-7

3-Methylthymidin

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction;88%
2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyluridine
87817-95-6

2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyluridine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With trifluoroacetic acid for 19h; Ambient temperature;87%
1,2,3,5-tetra-O-acetyl-β-L-ribofuranose
144490-03-9

1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

2,4-bis(trimethylsiloxy)-5-methylpyrimidine
7288-28-0

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
Stage #1: 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose; 2,4-bis(trimethylsiloxy)-5-methylpyrimidine With tin(IV) chloride In dichloromethane for 12h; Reflux;
Stage #2: With acetic acid In dichloromethane at 20℃; for 1h;
Stage #3: With ammonia In methanol at 20℃; for 12h;
85.06%
thymin
65-71-4

thymin

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With purine nucleoside phosphorylase; uridine phosphorylase at 90℃; for 48h; pH=9; aq. phosphate buffer; Enzymatic reaction;85%
In water; dimethyl sulfoxide at 25℃; pH=7.4; aq. phosphate buffer; Enzymatic reaction;79.1%
(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

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 6h; Inert atmosphere; Schlenk technique;81%
With ammonia In methanol at 20℃;
With Amberlite IRA 120 H+ In 1,4-dioxane; methanol14.1 g
5-(2,5-dimethoxythiophenyl)-5-methyl-5,6-dihydrouridine
1391764-47-8

5-(2,5-dimethoxythiophenyl)-5-methyl-5,6-dihydrouridine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
In water for 0.0666667h; Photolysis;78%
thymin
65-71-4

thymin

inosine
58-63-9

inosine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With potassium phosphate; xanthine oxidase; purine and pyrimidine nucleoside phosphorylase (PUNP, PYNP) at 40℃; for 11h;76%
With potassium phosphate; xanthine oxidase; PUNP, PYNP at 40℃; for 11h; Equilibrium constant;76%
7-methylguanosine hydroiodide
81100-62-1

7-methylguanosine hydroiodide

thymin
65-71-4

thymin

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With potassium dihydrogenphosphate; E. coli purine nucleoside phosphorylase; E. coli uridine phosphorylase In aq. buffer at 20℃; for 20h; pH=7.5; Enzymatic reaction;75%
stavudin
3056-17-5

stavudin

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With osmium(VIII) oxide In pyridine; N,N-dimethyl-formamide; benzene for 1.5h; Ambient temperature;74%
thymin
65-71-4

thymin

A

2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With mutant Escherichia coli uridine phosphorylase Lys235Arg, Gln236Ala; purine nucleoside phosphorylase from Bacillus halodurans at 60℃; for 2h; pH=7; Kinetics; Reagent/catalyst; Temperature; aq. buffer; Enzymatic reaction;A n/a
B 73.1%
5-(p-tolylthiomethyl)uridine

5-(p-tolylthiomethyl)uridine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With nickel In ethanol Heating;65%
2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine
64898-15-3

2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine

methyl iodide
74-88-4

methyl iodide

A

6-methyluridine
16710-13-7

6-methyluridine

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
Yield given. Multistep reaction;A n/a
B 61%
Yield given. Multistep reaction;A 4%
B n/a
thymin
65-71-4

thymin

Inosine
58-63-9

Inosine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
BM-11 E. coli cells, 0.015 M potassium phosphate buffer (pH 7.25); 1.) 60 deg C, 2 h, 2.) 4 deg C, 18 h;45%
thymin
65-71-4

thymin

α-D-ribofuranosyl-1-phosphate
18646-11-2

α-D-ribofuranosyl-1-phosphate

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
uridine phosphorylase;45%
(S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine
214039-19-7

(S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine

A

3-N-ethyl-5-methyluridine

3-N-ethyl-5-methyluridine

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With potassium fluoride In N,N-dimethyl-formamide at 130℃; for 6h; Ring cleavage; desilylation;A 35%
B 39%
5,S2-Dimethyl-2',3',5'-tri-O-acetyl-2-thiouridine
175875-24-8

5,S2-Dimethyl-2',3',5'-tri-O-acetyl-2-thiouridine

A

5-Methyluridine
1463-10-1

5-Methyluridine

B

2,5'-Anhydro-5-methyluridine
29789-17-1

2,5'-Anhydro-5-methyluridine

Conditions
ConditionsYield
With ammonium hydroxide at 55℃;A 25%
B 33%
5-(hydroxymethyl)uridine
30414-00-7

5-(hydroxymethyl)uridine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation;
trimethylaluminum
75-24-1

trimethylaluminum

1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-4-trimethylsilanyloxy-1H-pyrimidin-2-one
111582-94-6

1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-4-trimethylsilanyloxy-1H-pyrimidin-2-one

A

uridine
58-96-8

uridine

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With water; ammonium chloride; triphenylphosphine 1) THF, reflux, 10 h, 2) MeOH, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
With tetrakis(triphenylphosphine) palladium(0); water; ammonium chloride 1) THF, reflux, 2.5 h, 2) MeOH, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
trimethylaluminum
75-24-1

trimethylaluminum

1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-4-trimethylsilanyloxy-1H-pyrimidin-2-one
111582-84-4

1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-4-trimethylsilanyloxy-1H-pyrimidin-2-one

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With water; ammonium chloride; triphenylphosphine 1) THF, reflux, 4 h, 2) MeOH, reflux, 3 h; Yield given. Multistep reaction;
orotate anion
73-97-2

orotate anion

C10H14N2O6(1-)

C10H14N2O6(1-)

A

2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid anion
73-97-2

2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid anion

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.5;
N-methylnicotineamide iodide
6456-44-6

N-methylnicotineamide iodide

C10H14N2O6(1-)

C10H14N2O6(1-)

A

C7H9N2O
42986-37-8

C7H9N2O

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.4-8.7;
1-methyl-4-carboxypyridinium chloride
5746-18-9

1-methyl-4-carboxypyridinium chloride

C10H14N2O6(1-)

C10H14N2O6(1-)

A

C7H8NO2
36455-39-7

C7H8NO2

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
In water at 20℃; Rate constant; Equilibrium constant; pH 8.4-8.7;
2',3'-O,O-isopropylidene-5-methyluridine
2073-43-0

2',3'-O,O-isopropylidene-5-methyluridine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With trifluoroacetic acid Yield given;
Multi-step reaction with 5 steps
1.1: 5% rhodium on alumina; hydrogen / methanol / 12 h / 4654.46 Torr
2.1: pyridine; silver nitrate; triethylamine / tetrahydrofuran / 4 h
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
3.2: 0.42 h / -78 °C
4.1: trifluoroacetic acid / water / 1.5 h
5.1: water / 0.07 h / Photolysis
View Scheme
terephthalaldehyde,
623-27-8

terephthalaldehyde,

C10H14N2O6(1-)

C10H14N2O6(1-)

A

Benzene-1,4-dicarbaldehyde
623-27-8

Benzene-1,4-dicarbaldehyde

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
In water at 20℃; Rate constant; pH 8.4-8.7;
N-methyl-4-methylpyridinium iodide
2301-80-6

N-methyl-4-methylpyridinium iodide

C10H14N2O6(1-)

C10H14N2O6(1-)

A

1,4-dimethylpyridinyl radical

1,4-dimethylpyridinyl radical

B

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
In water at 20℃; Rate constant; Equilibrium constant; pH 8-8.5, var. pH;
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

5-Methyluridine
1463-10-1

5-Methyluridine

5′-O-tert-butyldiphenylsilyl-O2-2′-anhydro-5-methyluridine
134821-75-3

5′-O-tert-butyldiphenylsilyl-O2-2′-anhydro-5-methyluridine

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 18h; Inert atmosphere;100%
With pyridine at 20℃; for 24h; silylation;
With 1H-imidazole In N,N-dimethyl-formamide Molecular sieve; Inert atmosphere;
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
69304-37-6

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

5-Methyluridine
1463-10-1

5-Methyluridine

1-[(6aR,8R,9S,9aR)-tetrahydro-9-hydroxy-2,2,4,4-tetraisopropyl-6H-furo[3,2-f]-[1,3,5,2,4]trioxadisilocin-8-yl](5-methylpyrimidine)-2.4(1H.3H)-dione
130983-87-8

1-[(6aR,8R,9S,9aR)-tetrahydro-9-hydroxy-2,2,4,4-tetraisopropyl-6H-furo[3,2-f]-[1,3,5,2,4]trioxadisilocin-8-yl](5-methylpyrimidine)-2.4(1H.3H)-dione

Conditions
ConditionsYield
With pyridine for 6h; Ambient temperature;98%
In pyridine for 15h; Ambient temperature;84%
With pyridine80%
Acetyl bromide
506-96-7

Acetyl bromide

5-Methyluridine
1463-10-1

5-Methyluridine

1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine
110483-43-7

1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine

Conditions
ConditionsYield
In acetonitrile Heating;97%
With Trimethyl orthoacetate; hydrogen bromide 1.) acetic acid, 50 deg C, 1 h, 2.) 50 - 60 deg C, 5 h; Yield given. Multistep reaction;
acetic anhydride
108-24-7

acetic anhydride

5-Methyluridine
1463-10-1

5-Methyluridine

(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

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
With dmap; triethylamine In acetonitrile for 1h; Ambient temperature;97%
With pyridine for 10h; Ambient temperature;94%
With pyridine; dmap at 20℃; for 12h;90%
With pyridine at 0℃; for 5h;
Diethyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester
84416-80-8

Diethyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester

5-Methyluridine
1463-10-1

5-Methyluridine

C42H47N4O14P

C42H47N4O14P

Conditions
ConditionsYield
With 1H-tetrazole; silica gel In acetonitrile for 0.25h;97%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

5-Methyluridine
1463-10-1

5-Methyluridine

2′,3′,5′-tris(methanesulfonyl)-5-methyluridine
99614-96-7

2′,3′,5′-tris(methanesulfonyl)-5-methyluridine

Conditions
ConditionsYield
With 4-methyl-morpholine In acetone at 5 - 50℃; for 2.5h;97%
With triethylamine In dichloromethane at 20℃; for 0.00416667h; Reagent/catalyst; Temperature; Sonication; Flow reactor;97%
With 4-methyl-morpholine In acetone
4-Vinylphenylboronic acid
2156-04-9

4-Vinylphenylboronic acid

5-Methyluridine
1463-10-1

5-Methyluridine

C18H19BN2O6
1085524-26-0

C18H19BN2O6

Conditions
ConditionsYield
In 1,4-dioxane for 10h; Reflux;97%
benzoyl cyanide
613-90-1

benzoyl cyanide

5-Methyluridine
1463-10-1

5-Methyluridine

2',3',5'-tri-O-benzoyluridine
3180-76-5

2',3',5'-tri-O-benzoyluridine

Conditions
ConditionsYield
With dmap; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate at 25 - 35℃;96%
With dmap In various solvent(s) at 25 - 30℃; for 1.5h;96%
With pyridine; dmap at 40℃; for 3h;89%
With triethylamine In 1,4-dioxane at 20℃; for 0.666667h;70%
5-Methyluridine
1463-10-1

5-Methyluridine

O-2,2'-cyclo-5-methyluridine
22423-26-3

O-2,2'-cyclo-5-methyluridine

Conditions
ConditionsYield
With sodium hydroxide; Diethyl carbonate In N,N-dimethyl-formamide at 120℃; for 8h; Reagent/catalyst;95.6%
With bis(phenyl) carbonate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃;90%
With bis(phenyl) carbonate; sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) for 1h; Heating / reflux;85%
Dimethyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester
78635-91-3

Dimethyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester

5-Methyluridine
1463-10-1

5-Methyluridine

C42H47N4O14P

C42H47N4O14P

Conditions
ConditionsYield
With 1H-tetrazole; silica gel In acetonitrile for 0.25h; Product distribution; other reagent, other amount of reagent;95%
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

5-Methyluridine
1463-10-1

5-Methyluridine

2',3'-O,O-isopropylidene-5-methyluridine
2073-43-0

2',3'-O,O-isopropylidene-5-methyluridine

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 24h;95%
92%
With toluene-4-sulfonic acid In acetone at 20℃;58%
1,1-dimethoxycyclopentane
931-94-2

1,1-dimethoxycyclopentane

5-Methyluridine
1463-10-1

5-Methyluridine

1-(2'-O,3'-O-Cyclopentyl-5'-hydroxy-β-D-erythro-pentofuranosyl)-5-methyluracil
161824-82-4

1-(2'-O,3'-O-Cyclopentyl-5'-hydroxy-β-D-erythro-pentofuranosyl)-5-methyluracil

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 65℃; for 1.33333h;95%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

5-Methyluridine
1463-10-1

5-Methyluridine

2',3'-O-methoxyethylidene-5-methyluridine

2',3'-O-methoxyethylidene-5-methyluridine

Conditions
ConditionsYield
With acetic acid at 50℃; for 1h;95%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

5-Methyluridine
1463-10-1

5-Methyluridine

2',3'-O-methoxyethylidene-5-methyluridine

2',3'-O-methoxyethylidene-5-methyluridine

Conditions
ConditionsYield
In chloroform; acetic acid95%
benzylamine hydrochloride
3287-99-8, 39110-74-2

benzylamine hydrochloride

5-Methyluridine
1463-10-1

5-Methyluridine

(2'R,6'R)-2'-thymin-1-yl-6'-hydroxymethyl-N-benzyl morpholine
1221295-59-5

(2'R,6'R)-2'-thymin-1-yl-6'-hydroxymethyl-N-benzyl morpholine

Conditions
ConditionsYield
Stage #1: benzylamine hydrochloride; 5-Methyluridine With sodium periodate; sodium tetraborate decahydrate In methanol for 2.5h;
Stage #2: With sodium cyanoborohydride; triethylamine In methanol for 1h;
Stage #3: With trifluoroacetic acid In methanol for 3h;
95%
acetone
67-64-1

acetone

5-Methyluridine
1463-10-1

5-Methyluridine

2',3'-O,O-isopropylidene-5-methyluridine
2073-43-0

2',3'-O,O-isopropylidene-5-methyluridine

Conditions
ConditionsYield
With sulfuric acid; copper(II) sulfate for 48h; sealed bottle;94%
With sulfuric acid at 0 - 20℃;91%
With sulfuric acid; copper(II) sulfate75%
4-heptanone
123-19-3

4-heptanone

5-Methyluridine
1463-10-1

5-Methyluridine

1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dipropyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dipropyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 25h;94%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

5-Methyluridine
1463-10-1

5-Methyluridine

1-[5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine
119794-52-4

1-[5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 18h; Inert atmosphere;93%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;85%
With 1H-imidazole In N,N-dimethyl-formamide for 20h;73%
With 1H-imidazole In dichloromethane at 20℃; for 48h;50%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

5-Methyluridine
1463-10-1

5-Methyluridine

C52H92N2O9

C52H92N2O9

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Inert atmosphere;93%
1-Bromo-2-chloroethane
107-04-0

1-Bromo-2-chloroethane

5-Methyluridine
1463-10-1

5-Methyluridine

3-(2-chloroethyl)-2'-hydroxythymidine
1085484-19-0

3-(2-chloroethyl)-2'-hydroxythymidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.05h; microwave irradiation;92%
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

5-Methyluridine
1463-10-1

5-Methyluridine

2',3'-O-cyclohexylidene-5-methyluridine
1191255-79-4

2',3'-O-cyclohexylidene-5-methyluridine

Conditions
ConditionsYield
Stage #1: cycloxexanone dimethyl ketal; 5-Methyluridine With toluene-4-sulfonic acid In tetrahydrofuran for 0.5h; Reflux;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;
92%
With camphor-10-sulfonic acid In 1,2-dichloro-ethane for 2h; Reflux; Inert atmosphere;
5-Methyluridine
1463-10-1

5-Methyluridine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2',3'-di-O-methoxymethylidene-5-methyluridine
79137-02-3

2',3'-di-O-methoxymethylidene-5-methyluridine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃;91%
di-tert-butylsilyl bis(trifluoromethanesulfonate)
85272-31-7

di-tert-butylsilyl bis(trifluoromethanesulfonate)

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

5-Methyluridine
1463-10-1

5-Methyluridine

1-[2,2-di-tert-butyl-7-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-6-yl]-5-methyl-1H-pyrimidine-2,4-dione
922508-15-4

1-[2,2-di-tert-butyl-7-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-6-yl]-5-methyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
Stage #1: di-tert-butylsilyl bis(trifluoromethanesulfonate); 5-Methyluridine In N,N-dimethyl-formamide at 20℃;
Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
91%
benzoic acid anhydride
93-97-0

benzoic acid anhydride

5-Methyluridine
1463-10-1

5-Methyluridine

2',3',5'-tri-O-benzoyluridine
3180-76-5

2',3',5'-tri-O-benzoyluridine

Conditions
ConditionsYield
With dmap In various solvent(s) at 50℃; for 2h;90%
di-tert-butylsilyl bis(trifluoromethanesulfonate)
85272-31-7

di-tert-butylsilyl bis(trifluoromethanesulfonate)

5-Methyluridine
1463-10-1

5-Methyluridine

1-((4aR,6R,7R,7aS)-2,2-di-tert-butyl-7-hydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((4aR,6R,7R,7aS)-2,2-di-tert-butyl-7-hydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;90%
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere;90%

Ribosylthymine Chemical Properties

Molecule structure of 5-Methyluridine (CAS NO.1463-10-1):

IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 
Molecular Weight: 258.22796 g/mol
Molecular Formula: C10H14N2O6 
Density: 1.576 g/cm3 
Melting Point: 183-184 °C(lit.)
Index of Refraction: 1.618
Molar Refractivity: 57.43 cm3
Molar Volume: 163.7 cm3
Surface Tension: 75.9 dyne/cm 
Storage Temp.: 2-8 °C
XLogP3: -1.6
H-Bond Donor: 4
H-Bond Acceptor: 6
Rotatable Bond Count: 2
Tautomer Count: 3
Exact Mass: 258.085186
MonoIsotopic Mass: 258.085186
Topological Polar Surface Area: 119
Heavy Atom Count: 18
Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChI: InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1
InChIKey: DWRXFEITVBNRMK-JXOAFFINSA-N
EINECS: 215-973-9
Product Categories: Pyridines, Pyrimidines, Purines and Pteredines; Miscellaneous Biochemicals; Nucleotides and Nucleosides; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Nucleotides

Ribosylthymine Safety Profile

Hazard Codes: VeryT+
Risk Statements: 26/27/28 
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 24/25 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Ribosylthymine Specification

 5-Methyluridine (CAS NO.1463-10-1) is also named as Ribothymidine ; Thymine riboside ; Uridine, 5-methyl- . 5-Methyluridine (CAS NO.1463-10-1) is white powder. The stability of 5-methyluridine under standard temperature and pressure (STP) is very high.

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