5'-O-(tert-butyldiphenylsilyl)-2',3'-O-(isopropylidene)pseudouridine
pseudouridine
Conditions | Yield |
---|---|
With trifluoroacetic acid at 20℃; for 1h; | 100% |
pseudouridine
Conditions | Yield |
---|---|
at 70℃; for 2h; pH=9; | 100% |
5-(2,3-O-isopropylidene-β-D-ribofuranosyl)uracil
pseudouridine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 20℃; for 5h; | 93% |
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
pseudouridine
Conditions | Yield |
---|---|
With acetic acid at 50℃; for 5h; | 93% |
(2S,3S,4R,5R)-2-(2,4-dimethoxypyrimidin-5-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol
pseudouridine
Conditions | Yield |
---|---|
With acetic acid; sodium iodide for 0.75h; Inert atmosphere; Reflux; | 90% |
5-((3S,4R,5R)-3,4-Dimethoxy-5-methoxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
A
pseudouridine
B
α-pseudouridine
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -78℃; for 144h; | A 53% B n/a |
5-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
A
pseudouridine
B
α-pseudouridine
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -78℃; | A 42% B n/a |
With boron trichloride In dichloromethane at -78℃; Yields of byproduct given; |
(1S)-tri-O-acetyl-1-(2,4-bis-methylsulfanyl-pyrimidin-5-yl)-D-1,4-anhydro-ribitol
pseudouridine
Conditions | Yield |
---|---|
(i) MCPBA, (ii) H2O, (iii) NaOMe, MeOH; Multistep reaction; |
(1Ξ)-O2,O4;O3,O5-(R,R)-dibenzylidene-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-D-ribitol
A
(Ξ)-5-ξ-D-ribopyranosyl-pyrimidine-2,4-dione
B
pseudouridine
C
α-pseudouridine
Conditions | Yield |
---|---|
(i) BBr3, THF, (ii) MeOH, CH2Cl2; Multistep reaction; |
(2S,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,4-di-tert-butoxy-pyrimidin-5-yl)-pentane-1,4-diol
A
pseudouridine
B
α-pseudouridine
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -78℃; for 18h; |
5'-O-(tert-butyldiphenylsilyl)pseudouridine
pseudouridine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 4h; Desilylation; |
2,3-O-isopropylidene-5-O-(1-methoxy-1-methyl-ethyl)-D-ribono-1,4-lactone
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / tetrahydrofuran / -78 °C 2: 85 percent / L-Selectride; ZnCl2 / CH2Cl2; tetrahydrofuran; diethyl ether / -78 - 20 °C 3: 70 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 4 °C 4: 93 percent / aq. acetic acid / 5 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 94 percent / pyridinium p-toluenesulfonate; sodium sulfate / 1 h / 60 °C 2: 89 percent / tetrahydrofuran / -78 °C 3: 85 percent / L-Selectride; ZnCl2 / CH2Cl2; tetrahydrofuran; diethyl ether / -78 - 20 °C 4: 70 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 4 °C 5: 93 percent / aq. acetic acid / 5 h / 50 °C View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / L-Selectride; ZnCl2 / CH2Cl2; tetrahydrofuran; diethyl ether / -78 - 20 °C 2: 70 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 4 °C 3: 93 percent / aq. acetic acid / 5 h / 50 °C View Scheme |
(R)-1-{(4R,5S)-5-[(R)-(2,4-Di-tert-butoxy-pyrimidin-5-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(1-methoxy-1-methyl-ethoxy)-ethanol
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 4 °C 2: 93 percent / aq. acetic acid / 5 h / 50 °C View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: CH3COOH / 1 h / Heating 2: NaI / acetic acid / 0.42 h / Heating 3: HCl / methanol / 4 h View Scheme |
(2R,3S,4R,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dimethoxy-pyrimidin-5-yl)-tetrahydro-furan-3,4-diol
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaI / acetic acid / 0.42 h / Heating 2: HCl / methanol / 4 h View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: BF3*Et2O; Et3SiH / CH2Cl2 / 1 h / 4 °C / 20 deg C 2: NaI / acetic acid / 0.42 h / Heating 3: HCl / methanol / 4 h View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 60 percent / C2H5ONa / ethanol / 5 h / Heating 2: 93 percent / HCl / methanol / 5 h / 20 °C View Scheme |
2-(2,4:3,5-di-O-benzylidenepentitol-1-yl)pyridine
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) nBuLi, THF, (ii) /BRN= 1260242/ 2: (i) BBr3, THF, (ii) MeOH, CH2Cl2 View Scheme |
2-methylsulfanyl-pyrimidin-4-yl tri-O-acetyl-β-D-1-thio-ribofuranoside
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) (UV-irradiation), (ii) /BRN= 969135/ 2: (i) MCPBA, (ii) H2O, (iii) NaOMe, MeOH View Scheme |
pseudoisocytidine
pseudouridine
Conditions | Yield |
---|---|
With acetic anhydride In pyridine; ethyl acetate | 3.2 g (85%) |
Conditions | Yield |
---|---|
With bacterial pseudouridine synthase TruB In aq. buffer at 37℃; Kinetics; Reagent/catalyst; Enzymatic reaction; |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1H-imidazole / dichloromethane / 0 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 °C 3: triethylamine / dichloromethane / 1 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 48 h / 0 - 75 °C 5: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / -20 °C 6: sodium iodide; acetic acid / 0.75 h / Inert atmosphere; Reflux View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 °C 2: triethylamine / dichloromethane / 1 h / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 48 h / 0 - 75 °C 4: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / -20 °C 5: sodium iodide; acetic acid / 0.75 h / Inert atmosphere; Reflux View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 48 h / 0 - 75 °C 3: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / -20 °C 4: sodium iodide; acetic acid / 0.75 h / Inert atmosphere; Reflux View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 48 h / 0 - 75 °C 2: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / -20 °C 3: sodium iodide; acetic acid / 0.75 h / Inert atmosphere; Reflux View Scheme |
pseudouridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / -20 °C 2: sodium iodide; acetic acid / 0.75 h / Inert atmosphere; Reflux View Scheme |
Conditions | Yield |
---|---|
In ethanol for 16h; pH=8.5; triethylammoniumbicarbonate buffer; | 98% |
With formic acid; triethylamine In ethanol; water for 16h; pH=8.5; | 98% |
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In ethanol for 16h; | 98% |
In ethanol for 16h; Triethylammonium-bicarbonate buffer; | 98% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
pseudouridine
3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)pseudouridine
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; | 97.8% |
In pyridine at 20℃; Cooling with ice; | 97.8% |
With pyridine at 0 - 20℃; | 94% |
acetic anhydride
pseudouridine
5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at -30℃; for 3h; | 95% |
With pyridine at 20℃; | 92% |
With pyridine Ambient temperature; |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 24h; Michael Addition; regioselective reaction; | 92% |
tert-butyldimethylsilyl chloride
pseudouridine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide | 90% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 24h; Reagent/catalyst; Michael Addition; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 24h; Michael Addition; regioselective reaction; | 88% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 24h; Michael Addition; regioselective reaction; | 87% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 24h; Michael Addition; regioselective reaction; | 86% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 36h; Michael Addition; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 36h; Michael Addition; regioselective reaction; | 85% |
acrylonitrile
pseudouridine
A
C15H18N4O6
B
Monocyanoethylpseudouridin
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 24h; | A 9% B 84% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 36h; Michael Addition; regioselective reaction; | 84% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 36h; Michael Addition; regioselective reaction; | 82% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 36h; Michael Addition; regioselective reaction; | 82% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 48h; Michael Addition; regioselective reaction; | 77% |
N,N-dimethyl-formamide dimethyl acetal
pseudouridine
1,3-dimethyl-Ψ-uridine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 110℃; for 1h; | 75.4% |
In dimethyl sulfoxide at 110℃; for 1h; | 75.4% |
Heating; | |
at 110℃; for 1h; | |
at 110℃; for 1h; |
4,4'-dimethoxytrityl chloride
pseudouridine
Conditions | Yield |
---|---|
With pyridine for 14h; Ambient temperature; | 73% |
With pyridine at 20℃; for 2h; | 58% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 24h; | 66% |
pseudouridine
mono-4-methoxytrityl chloride
Conditions | Yield |
---|---|
With pyridine at 20℃; for 15h; | 58% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 57% |
N-(3-iodopropyl)phthalimide
pseudouridine
A
C20H21N3O8
B
C31H30N4O10
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; | A 25% B 37% |
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
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