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Basic Information
CAS No.: 1445-07-4
Name: BETA-PSEUDOURIDINE
Article Data: 21
Molecular Structure:
Molecular Structure of 1445-07-4 (BETA-PSEUDOURIDINE)
Formula: C9H12N2O6
Molecular Weight: 244.204
Synonyms: Uracil,5-b-D-ribofuranosyl- (6CI,7CI,8CI);5-(b-D-Ribofuranosyl)uracil;5-Ribosyluracil;NSC 162405;Pseudouridine;Pseudouridine C;b-D-Pseudouridine;b-Pseudouridine;y-Uridine;
Density: 1.641 g/cm3
Melting Point: 222 °C
Boiling Point: 598.4 °C at 760 mmHg
Flash Point: 315.7 °C
PSA: 135.64000
LogP: -2.78280
Synthetic route
1024616-70-3

5'-O-(tert-butyldiphenylsilyl)-2',3'-O-(isopropylidene)pseudouridine

1445-07-4

pseudouridine

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 1h;100%

C9H13N2O9S(1-)*Na(1+)

1445-07-4

pseudouridine

Conditions
ConditionsYield
at 70℃; for 2h; pH=9;100%
28113-58-8

5-(2,3-O-isopropylidene-β-D-ribofuranosyl)uracil

1445-07-4

pseudouridine

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 5h;93%
631920-69-9

2,4-Di-tert-butoxy-5-[(3aS,4S,6R,6aR)-6-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrimidine

1445-07-4

pseudouridine

Conditions
ConditionsYield
With acetic acid at 50℃; for 5h;93%
68168-19-4

(2S,3S,4R,5R)-2-(2,4-dimethoxypyrimidin-5-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol

1445-07-4

pseudouridine

Conditions
ConditionsYield
With acetic acid; sodium iodide for 0.75h; Inert atmosphere; Reflux;90%
78119-28-5, 78119-29-6

5-((3S,4R,5R)-3,4-Dimethoxy-5-methoxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

A

1445-07-4

pseudouridine

B

10017-66-0

α-pseudouridine

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78℃; for 144h;A 53%
B n/a
78119-26-3, 78119-27-4

5-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

A

1445-07-4

pseudouridine

B

10017-66-0

α-pseudouridine

Conditions
ConditionsYield
With boron trichloride In dichloromethane at -78℃;A 42%
B n/a
With boron trichloride In dichloromethane at -78℃; Yields of byproduct given;
64714-46-1

(1S)-tri-O-acetyl-1-(2,4-bis-methylsulfanyl-pyrimidin-5-yl)-D-1,4-anhydro-ribitol

1445-07-4

pseudouridine

Conditions
ConditionsYield
(i) MCPBA, (ii) H2O, (iii) NaOMe, MeOH; Multistep reaction;
67320-14-3, 67320-15-4

(1Ξ)-O2,O4;O3,O5-(R,R)-dibenzylidene-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-D-ribitol

A

20337-08-0, 67375-32-0

(Ξ)-5-ξ-D-ribopyranosyl-pyrimidine-2,4-dione

B

1445-07-4

pseudouridine

C

10017-66-0

α-pseudouridine

Conditions
ConditionsYield
(i) BBr3, THF, (ii) MeOH, CH2Cl2; Multistep reaction;
78119-22-9, 78119-23-0

(2S,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,4-di-tert-butoxy-pyrimidin-5-yl)-pentane-1,4-diol

A

1445-07-4

pseudouridine

B

10017-66-0

α-pseudouridine

Conditions
ConditionsYield
With boron trichloride In dichloromethane at -78℃; for 18h;
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Specification

The Pseudouridine is an organic compound with the formula C9H12N2O6. The IUPAC name of this chemical is 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidine-2,4-dione. With the CAS registry number 1445-07-4, it is also named as 2,4(1H,3H)-Pyrimidinedione, 5-β-D-ribofuranosyl-. Besides, it may offer protection from radiation.

Physical properties about Pseudouridine are: (1)ACD/LogP: -0.37; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.37; (4)ACD/LogD (pH 7.4): -0.41; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 14.94; (8)ACD/KOC (pH 7.4): 13.82; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 77.54 Å2; (13)Index of Refraction: 1.623; (14)Molar Refractivity: 52.5 cm3; (15)Molar Volume: 148.7 cm3; (16)Polarizability: 20.81×10-24cm3; (17)Surface Tension: 80.3 dyne/cm; (18)Density: 1.641 g/cm3; (19)Flash Point: 315.7 °C; (20)Enthalpy of Vaporization: 93.71 kJ/mol; (21)Boiling Point: 598.4 °C at 760 mmHg; (22)Vapour Pressure: 3.63E-15 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1N\C=C(/C(=O)N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
(2)InChI: InChI=1/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/m1/s1
(3)InChIKey: PTJWIQPHWPFNBW-GBNDHIKLBY
(4)Std. InChI: InChI=1S/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/m1/s1
(5)Std. InChIKey: PTJWIQPHWPFNBW-GBNDHIKLSA-N