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[ CAS No. 54-25-1 ] {[proInfo.proName]}

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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 54-25-1
Chemical Structure| 54-25-1
Structure of 54-25-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54-25-1 ]

CAS No. :54-25-1 MDL No. :MFCD00006472
Formula : C8H11N3O6 Boiling Point : -
Linear Structure Formula :- InChI Key :WYXSYVWAUAUWLD-SHUUEZRQSA-N
M.W : 245.19 Pubchem ID :5901
Synonyms :

Calculated chemistry of [ 54-25-1 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.62
Num. rotatable bonds : 2
Num. H-bond acceptors : 7.0
Num. H-bond donors : 4.0
Molar Refractivity : 52.06
TPSA : 137.67 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.32
Log Po/w (XLOGP3) : -2.14
Log Po/w (WLOGP) : -3.78
Log Po/w (MLOGP) : -2.52
Log Po/w (SILICOS-IT) : -1.86
Consensus Log Po/w : -2.0

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.14
Solubility : 177.0 mg/ml ; 0.723 mol/l
Class : Very soluble
Log S (Ali) : -0.22
Solubility : 147.0 mg/ml ; 0.6 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 1.12
Solubility : 3210.0 mg/ml ; 13.1 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.88

Safety of [ 54-25-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280 UN#:2811
Hazard Statements:H302-H312-H332-H350 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 54-25-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 54-25-1 ]

[ 54-25-1 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 613-90-1 ]
  • [ 54-25-1 ]
  • [ 54898-50-9 ]
YieldReaction ConditionsOperation in experiment
(i) NaHCO3, diphenyl carbonate, HMPT, (ii) /BRN= 1072101/, Et3N, MeCN; Multistep reaction;
  • 3
  • [ 75-44-5 ]
  • [ 54-25-1 ]
  • [ 69244-30-0 ]
  • [ 59967-97-4 ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 12% In N,N,N,N,N,N-hexamethylphosphoric triamide; toluene for 5.5h; Ambient temperature;
  • 4
  • [ 54-25-1 ]
  • Lithium; (3aR,4R,6R,6aR)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-hydroxymethyl-2-oxo-tetrahydro-2λ5-furo[3,4-d][1,3,2]dioxaphosphol-2-olate [ No CAS ]
  • [ 32350-72-4 ]
YieldReaction ConditionsOperation in experiment
27.3% With ribonuclease A In water for 120h; 1) -30 deg C (addition); 2) -10 deg C;
  • 5
  • [ 54-25-1 ]
  • [ 58337-35-2 ]
  • [ 102420-06-4 ]
  • [ 102420-08-6 ]
YieldReaction ConditionsOperation in experiment
for 0.0833333h; Ambient temperature; 1 M H2O2, 0.01 mM horseradish peroxidase (HRP), 0.05 M phosphate buffer (pH 8); Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 6
  • [ 54-25-1 ]
  • [ 149-73-5 ]
  • 2',3'-O-methoxymethylidene-6-azauridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silica gel; toluene-4-sulfonic acid 1.) room temperature, 2.) CH3OH/CH2Cl2, 3 days; Yield given. Multistep reaction;
  • 7
  • [ 54-25-1 ]
  • [ 69244-33-3 ]
YieldReaction ConditionsOperation in experiment
59% With thionyl chloride In N,N,N,N,N,N-hexamethylphosphoric triamide for 2h; Ambient temperature;
  • 8
  • [ 54-25-1 ]
  • [ 69244-33-3 ]
  • (SR)-5'-chloro-5'-deoxy-2',3'-O-sulfinyl-6-azauridine [ No CAS ]
  • (SS)-5'-chloro-5'-deoxy-2',3'-O-sulfinyl-6-azauridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 13% 2: 18% 3: 6.1% With N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride for 1h; Ambient temperature;
  • 9
  • [ 54-25-1 ]
  • [ 530-62-1 ]
  • [ 69244-31-1 ]
  • [ 69244-30-0 ]
  • [ 59967-97-4 ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 32% In N,N-dimethyl-formamide for 24h; Ambient temperature;
  • 10
  • [ 59967-97-4 ]
  • [ 54-25-1 ]
YieldReaction ConditionsOperation in experiment
89% In pyridine; water at 100℃; for 0.75h;
  • 11
  • [ 40615-36-9 ]
  • [ 54-25-1 ]
  • [ 108-24-7 ]
  • 5'-O-dimethoxytrityl-2',3'-di-O-acetyl-6-aza-uridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.) pyridine, 2.) pyridine; Yield given. Multistep reaction;
  • 12
  • [ 40615-36-9 ]
  • [ 54-25-1 ]
  • [ 18162-48-6 ]
  • 2-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-2H-[1,2,4]triazine-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver nitrate 1.) pyridine, 2.) pyridine, THF; Multistep reaction;
  • 13
  • [ 54-25-1 ]
  • [ 122-51-0 ]
  • [ 95295-68-4 ]
YieldReaction ConditionsOperation in experiment
51% With toluene-4-sulfonic acid at 20 - 22℃; for 24h;
  • 15
  • [ 54-25-1 ]
  • 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazine-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen In acetic acid 3 weeks;
  • 16
  • [ 2169-64-4 ]
  • [ 54-25-1 ]
YieldReaction ConditionsOperation in experiment
95% With sodium methylate In methanol at 0℃; for 0.25h;
  • 17
  • [ 54-25-1 ]
  • [ 23541-50-6 ]
  • 2-((2R,6S)-6-Hydroxymethyl-4-{(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[(1S,3S)-3,5,12-trihydroxy-3-(1-hydroxy-ethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyran-4-yl}-morpholin-2-yl)-2H-[1,2,4]triazine-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetate; Dowex resin (1x8; sodium cyanoborohydride; sodium hydrogencarbonate; periodic acid 1.) H2O, rt, 2 h, 2.) H2O, rt, 3 h; Yield given. Multistep reaction;
  • 18
  • [ 54-25-1 ]
  • (R)-2-[(R)-1-(3,5-Dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-2-oxo-ethoxy]-3-hydroxy-propionaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Dowex resin (1x8, CH3CO2-); periodic acid In water for 6h; Ambient temperature; Yield given;
  • 20
  • [ 54-25-1 ]
  • [ 31281-61-5 ]
YieldReaction ConditionsOperation in experiment
52% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 21
  • [ 54-25-1 ]
  • [ 138779-22-3 ]
YieldReaction ConditionsOperation in experiment
23% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 22
  • [ 54-25-1 ]
  • [ 138779-19-8 ]
YieldReaction ConditionsOperation in experiment
63% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 23
  • [ 54-25-1 ]
  • [ 138779-20-1 ]
YieldReaction ConditionsOperation in experiment
64% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 24
  • [ 54-25-1 ]
  • [ 138779-21-2 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 25
  • [ 54-25-1 ]
  • [ 138779-23-4 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 26
  • [ 54-25-1 ]
  • [ 138779-25-6 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 27
  • [ 54-25-1 ]
  • [ 138779-26-7 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 28
  • [ 54-25-1 ]
  • [ 138779-28-9 ]
YieldReaction ConditionsOperation in experiment
22% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 29
  • [ 54-25-1 ]
  • [ 138779-24-5 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 30
  • [ 54-25-1 ]
  • [ 138779-27-8 ]
YieldReaction ConditionsOperation in experiment
37% With sodium hydroxide In dimethyl sulfoxide; acetone
  • 31
  • [ 54-25-1 ]
  • N3-phenacyl-6-azauridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With potassium carbonate In dimethyl sulfoxide; acetone
  • 32
  • o-methoxyphenacyl bromide [ No CAS ]
  • [ 54-25-1 ]
  • N3-(o-methoxyphenacyl)-2-β-D-ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With potassium carbonate In dimethyl sulfoxide; acetone
  • 33
  • m-methoxyphenacyl bromide [ No CAS ]
  • [ 54-25-1 ]
  • N3-(m-methoxyphenacyl)-2-β-D-ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With potassium carbonate In dimethyl sulfoxide; acetone
  • 34
  • 2',4'-dimethoxyphenacyl bromide [ No CAS ]
  • [ 54-25-1 ]
  • N3-(2',4'-dimethoxyphenacyl)-2-β-D-ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate In dimethyl sulfoxide; acetone
  • 35
  • 2',5'-dimethoxyphenacyl bromide [ No CAS ]
  • [ 54-25-1 ]
  • N3-(2',5'-dimethoxyphenacyl)-2-β-D-ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate In dimethyl sulfoxide; acetone
  • 36
  • p-methoxyphenacyl bromide [ No CAS ]
  • [ 54-25-1 ]
  • N3-(p-methoxyphenacyl)-2-β-D-ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In dimethyl sulfoxide; acetone
  • 37
  • [ 54-25-1 ]
  • [ 108-24-7 ]
  • [ 2169-64-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap at 20℃; for 2h;
  • 38
  • [ 54-25-1 ]
  • [ 2018-19-1 ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 6-Azauridine With pyridine; water; trichlorophosphate In acetonitrile at 0℃; for 5h; Stage #2: With water In acetonitrile for 1h;
  • 39
  • [ 54-25-1 ]
  • [ 389635-66-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / pyridine / 1 h / 0 - 20 °C 2: pyridinium p-toluenesulfonate / 55 °C 3: TEMED-HF / acetonitrile / 6 h / 20 °C
  • 40
  • [ 54-25-1 ]
  • Acetic acid 2-{(2-acetoxy-ethoxy)-[(2R,3R,3aR,9aR)-2-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-methoxy}-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / pyridine / 1 h / 0 - 20 °C 2: pyridinium p-toluenesulfonate / 55 °C
  • 41
  • [ 54-25-1 ]
  • [ 389635-67-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 97 percent / pyridine / 1 h / 0 - 20 °C 2: pyridinium p-toluenesulfonate / 55 °C 3: TEMED-HF / acetonitrile / 6 h / 20 °C 4: 58 percent / imidazole / tetrahydrofuran / 0.83 h / 0 °C
  • 42
  • [ 54-25-1 ]
  • C42H81N4O16PSi3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 97 percent / pyridine / 1 h / 0 - 20 °C 2: pyridinium p-toluenesulfonate / 55 °C 3: TEMED-HF / acetonitrile / 6 h / 20 °C 4: 58 percent / imidazole / tetrahydrofuran / 0.83 h / 0 °C 5: 59 percent / 1H-tetrazole / CH2Cl2 / 7 h / 20 °C
  • 43
  • [ 54-25-1 ]
  • [ 257297-86-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pyridine; DMAP / 2 h / 20 °C 2.1: phosphorus oxychloride; triethylamine / acetonitrile / 0.5 h / 0 °C 2.2: acetonitrile / 4 h / 0 - 20 °C
  • 44
  • [ 54-25-1 ]
  • 6-azacytidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pyridine; DMAP / 2 h / 20 °C 2.1: phosphorus oxychloride; triethylamine / acetonitrile / 0.5 h / 0 °C 2.2: acetonitrile / 4 h / 0 - 20 °C 3.1: 226 mg / NH4Cl; DBU / pyridine / 24 h / 20 °C 4.1: NH3 / methanol / 24 h / 20 °C
  • 45
  • [ 54-25-1 ]
  • 5'-O-(1-thio)-6-azacytidine triphosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridine; DMAP / 2 h / 20 °C 2.1: phosphorus oxychloride; triethylamine / acetonitrile / 0.5 h / 0 °C 2.2: acetonitrile / 4 h / 0 - 20 °C 3.1: 226 mg / NH4Cl; DBU / pyridine / 24 h / 20 °C 4.1: NH3 / methanol / 24 h / 20 °C
  • 46
  • [ 54-25-1 ]
  • [ 20757-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: pyridine; DMAP / 2 h / 20 °C 2.1: phosphorus oxychloride; triethylamine / acetonitrile / 0.5 h / 0 °C 2.2: acetonitrile / 4 h / 0 - 20 °C 3.1: 226 mg / NH4Cl; DBU / pyridine / 24 h / 20 °C
  • 47
  • [ 54-25-1 ]
  • [ 221171-43-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / pyridine / 72 h / Ambient temperature 2: 1.0 g / CrO3, pyridine / CH2Cl2 / 30 h / Ambient temperature
  • 48
  • [ 54-25-1 ]
  • [ 70834-10-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 43 percent / pyridine / 25 h / 0 - 4 °C 2: 77 percent / NaN3 / dimethylformamide / 6 h / 70 °C 3: 1.) (Ph)3P, 2.) 10N aq.NH4OH / 1.) pyridine, 3 h, 2.) pyridine, 2 h
  • 49
  • [ 54-25-1 ]
  • 5'-O-nicotinoyl-6-azauridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 51 percent / p-TsOH / 24 h / 20 - 22 °C 2: pyridine / 3 h / 40 - 50 °C 3: 64 percent / 80percent aq. AcOH / 1 h / Heating
  • 50
  • [ 54-25-1 ]
  • [ 70834-11-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 43 percent / pyridine / 25 h / 0 - 4 °C 2: 77 percent / NaN3 / dimethylformamide / 6 h / 70 °C
  • 51
  • [ 54-25-1 ]
  • [ 170936-95-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 51 percent / p-TsOH / 24 h / 20 - 22 °C 2: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 4 deg C, 24 h 3: 76 percent / NaN3 / dimethylformamide / 6 h / 70 °C
  • 52
  • [ 54-25-1 ]
  • 5'-nicotinamido-5'-deoxy-6-azauridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 43 percent / pyridine / 25 h / 0 - 4 °C 2: 77 percent / NaN3 / dimethylformamide / 6 h / 70 °C 3: 1.) (Ph)3P, 2.) 10N aq.NH4OH / 1.) pyridine, 3 h, 2.) pyridine, 2 h 4: 56 percent / H2O; ethanol / 20 h / 20 - 22 °C
  • 53
  • [ 54-25-1 ]
  • [ 170936-93-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 51 percent / p-TsOH / 24 h / 20 - 22 °C 2: pyridine / 3 h / 40 - 50 °C
  • 54
  • [ 54-25-1 ]
  • [ 170743-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 51 percent / p-TsOH / 24 h / 20 - 22 °C 2: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 4 deg C, 24 h 3: 76 percent / NaN3 / dimethylformamide / 6 h / 70 °C 4: 1.) (Ph)3P, 2.) 10N aq.NH4OH / 1.) pyridine, 3 h, 2.) pyridine, 2 h
  • 55
  • [ 54-25-1 ]
  • [ 170743-87-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 51 percent / p-TsOH / 24 h / 20 - 22 °C 2: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 4 deg C, 24 h
  • 56
  • [ 54-25-1 ]
  • [ 69244-32-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 62 percent / toluene; hexamethylphosphoric acid triamide / 5.5 h / Ambient temperature 2: 38 percent / CH3ONa, methanol / 0.5 h / Ambient temperature
  • 57
  • [ 54-25-1 ]
  • [ 114933-50-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 59 percent / thionylchloride / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 2: 38 percent / dimethylformamide / 1.5 h / Ambient temperature 3: 45 percent / imidazole / dimethylformamide / 12 h / 150 °C 4: 82 percent / hydrogen chloride / dimethylformamide / 3 h / 100 °C
  • 58
  • [ 54-25-1 ]
  • [ 73619-38-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / thionylchloride / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 2: 38 percent / dimethylformamide / 1.5 h / Ambient temperature
  • 59
  • [ 54-25-1 ]
  • [ 114933-51-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / thionylchloride / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 2: 61 percent / acetyl chloride / acetic acid / 24 h / Ambient temperature
  • 60
  • [ 54-25-1 ]
  • [ 69244-36-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 59 percent / thionylchloride / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 2: 38 percent / dimethylformamide / 1.5 h / Ambient temperature 3: 45 percent / imidazole / dimethylformamide / 12 h / 150 °C
  • 61
  • [ 54-25-1 ]
  • 3-(7β-hydroxycholesteryl) 5'-(6-azauridylyl) 2-cyanoethyl phosphotriester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) p-toluene sulphonic acid, 2.) silica gel / 1.) room temperature, 2.) CH3OH/CH2Cl2, 3 days 2: 1.) tetrazole, 2.) m-chloro perbenzoic acid (55percent) 3: 86 percent / 0.36percent HCl / tetrahydrofuran / 2 h / Ambient temperature
  • 62
  • [ 54-25-1 ]
  • 3-(7β-triethylsilyloxycholesteryl) 5'-(2',3'-methoxymethylidene-6-azauridylyl) 2-cyanoethyl phosphotriester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) p-toluene sulphonic acid, 2.) silica gel / 1.) room temperature, 2.) CH3OH/CH2Cl2, 3 days 2: 1.) tetrazole, 2.) m-chloro perbenzoic acid (55percent)
  • 63
  • [ 54-25-1 ]
  • [ 129836-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) p-toluene sulphonic acid, 2.) silica gel / 1.) room temperature, 2.) CH3OH/CH2Cl2, 3 days 2: 1.) tetrazole, 2.) m-chloro perbenzoic acid (55percent) 3: 86 percent / 0.36percent HCl / tetrahydrofuran / 2 h / Ambient temperature 4: 100 percent / 25percent aqueous ammonia / methanol / ion-exchange chromatography (Dowex-50 resin)
  • 64
  • [ 118170-03-9 ]
  • [ 54-25-1 ]
  • Ru(N-hydroxyethylethylenediamine-N,N',N'-triacetate)(C8H10N3O6)(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water-d2 absence of air; 2 equiv. of Ru-complex, > 15 h; not isolated, reaction followed by (1)H-NMR spectroscopy;
  • 65
  • [ 118170-03-9 ]
  • [ 54-25-1 ]
  • Ru(N-hydroxyethylethylenediaminetriacetate)(η(2)(5,6)-6-azauridine)(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diclazuril In water-d2 absence of air; 2 equiv. of Ru-complex, 15 h, then pH adjustment below 3.0 (DCl); not isolated, reaction followed by (1)H-NMR spectroscopy;
  • 66
  • [ 54-25-1 ]
  • [ 120-92-3 ]
  • [ 93475-80-0 ]
YieldReaction ConditionsOperation in experiment
33% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 4h;
  • 67
  • [ 54-25-1 ]
  • [ 95483-15-1 ]
  • 3-[(2R,3aR,4R,6R,6aR)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)tetrahydro-6-(hydroxymethyl)-2-methylfuro[3,4-d][1,3]dioxol-2-yl]propyl 4-methylbenzoate [ No CAS ]
  • 3-((4R,6R)-4-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-6-(hydroxymethyl)-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-2-yl)propyl 4-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.429 % de With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 24h; Overall yield = 100 %;
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide
  • 68
  • [ 54-25-1 ]
  • [ 539-88-8 ]
  • ethyl 3-[(2S,3aR,4R,6R,6aR)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-6-(hydroxymethyl)-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-2-yl]propanoate [ No CAS ]
  • [ 71765-35-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 25h; Overall yield = 54 %; Overall yield = 1.63 g;
  • 69
  • [ 504-57-4 ]
  • [ 54-25-1 ]
  • 2-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dinonyltetrahydrofuro[3,4-d] [1,3]dioxol-4-yl]-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at 20℃; for 75h;
  • 70
  • [ 54-25-1 ]
  • [(2R,3aR,4R,6R,6aR)-6-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-2-(3-ethoxy-3-oxopropyl)tetrahydro-2-methylfuro[3,4-d][1,3]dioxol-4-yl]methyl 2-propylpentanoate [ No CAS ]
  • 2-[2,3-O-((1S)-4-ethoxy-1-methyl-4-oxobutylidene)-5-O-(2-propylpentanoyl)-β-D–ribofuranosyl]-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane 2: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 21 h / 5 - 20 °C / Inert atmosphere
  • 71
  • [ 54-25-1 ]
  • (1S)-NL_3.1.1.0 [ No CAS ]
  • ethyl 3-{(2R,3aR,4R,6R,6aR)-4,5-dihydro-4-(hydroxymethyl)-2-methyl-6-[4-(3-methylbut-2-en-1-yl)-3,5-dioxo-1,2,4-triazin-2(3H)-yl]-tetrahydrofuro[3,4-d][1,3]dioxol-2-yl}propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 2.2: 22 h / 20 °C / Inert atmosphere
  • 72
  • [ 54-25-1 ]
  • (1S)-NL_3.1.2.0 [ No CAS ]
  • ethyl 3-[(2R,3aR,4R,6R,6aR)-4-{4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl}-6-(hydroxymethyl)-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-2-yl]propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 2.2: 24 h / 20 °C / Inert atmosphere
  • 73
  • [ 54-25-1 ]
  • (1S)-NL_3.1.0.1 [ No CAS ]
  • ethyl 3-[(2R,3aR,4R,6R,6aR)-4-[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-6-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-tetrahydro-2-methylfuro[3,4-d][1,3]dioxol-2-yl]propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane 2: pyridine / 24 h / 20 °C / Inert atmosphere
  • 74
  • [ 54-25-1 ]
  • 10-(4-[(2R,3aR,4R,6R,6aR)-6-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-2-(3-ethoxy-3-oxopropyl)tetrahydro-2-methylfuro[3,4-d][1,3]dioxol-4-yl]methoxy}-4-oxobutyl)-3,6-bis(dimethylamino)acridinium perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane 2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice; Darkness
  • 75
  • [ 54-25-1 ]
  • [ 870-63-3 ]
  • 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(3-methylbut-2-en-1-yl)-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 6-Azauridine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Inert atmosphere; Stage #2: prenyl bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
  • 76
  • [ 6138-90-5 ]
  • [ 54-25-1 ]
  • 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 6-Azauridine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Stage #2: trans-geranyl bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
  • 77
  • farnesyl bromide [ No CAS ]
  • [ 54-25-1 ]
  • 2-[(2R,3R,4S,5R)-tetrahydro-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.4% Stage #1: 6-Azauridine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Stage #2: farnesyl bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
  • 78
  • [ 502-72-7 ]
  • [ 54-25-1 ]
  • 2-[(3a'R,4'R,6'R,6a'R)-tetrahydro-6'-(hydroxymethyl)spiro[cyclopentadecane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl]-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 24h;
  • 79
  • [ 54-25-1 ]
  • [ 539-88-8 ]
  • ethyl 3-[(3aR,4R,6R,6aR)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-6-(hydroxymethyl)-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-2-yl]propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 24h;
  • 80
  • [ 4704-31-8 ]
  • [ 54-25-1 ]
  • 6-azauridine 5'-decanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 4h; Enzymatic reaction; regioselective reaction; Enzymatic acylation of nucleoside General procedure: In a typical experiment, 6-azauridine (0.04 mmol), C. antarctica lipase B and vinyl ester were added into 2 mL anhydrous organic solvent and the mixture was incubated at a predetermined temperature in an orbital air-bath shaker (200 rpm). Aliquots were withdrawn at specified time intervals from the reaction mixture and then diluted 50-fold with corresponding mobile phase priorto HPLC analysis. Regioselectivity was defined as the molar ratio of the desired product to the total amount of ester products formed. All data are averages of experiments performed in triplicate.
  • 81
  • [ 5809-91-6 ]
  • [ 54-25-1 ]
  • 6-azauridine 5'-myristate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 4.5h; Enzymatic reaction; regioselective reaction; Enzymatic acylation of nucleoside General procedure: In a typical experiment, 6-azauridine (0.04 mmol), C. antarctica lipase B and vinyl ester were added into 2 mL anhydrous organic solvent and the mixture was incubated at a predetermined temperature in an orbital air-bath shaker (200 rpm). Aliquots were withdrawn at specified time intervals from the reaction mixture and then diluted 50-fold with corresponding mobile phase priorto HPLC analysis. Regioselectivity was defined as the molar ratio of the desired product to the total amount of ester products formed. All data are averages of experiments performed in triplicate.
  • 82
  • [ 693-38-9 ]
  • [ 54-25-1 ]
  • 6-azauridine 5'-palmitate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 4.5h; Enzymatic reaction; regioselective reaction; Enzymatic acylation of nucleoside General procedure: In a typical experiment, 6-azauridine (0.04 mmol), C. antarctica lipase B and vinyl ester were added into 2 mL anhydrous organic solvent and the mixture was incubated at a predetermined temperature in an orbital air-bath shaker (200 rpm). Aliquots were withdrawn at specified time intervals from the reaction mixture and then diluted 50-fold with corresponding mobile phase priorto HPLC analysis. Regioselectivity was defined as the molar ratio of the desired product to the total amount of ester products formed. All data are averages of experiments performed in triplicate.
  • 83
  • [ 5299-57-0 ]
  • [ 54-25-1 ]
  • 6-azauridine 5'-10-undecenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 4h; Enzymatic reaction; regioselective reaction; Enzymatic acylation of nucleoside General procedure: In a typical experiment, 6-azauridine (0.04 mmol), C. antarctica lipase B and vinyl ester were added into 2 mL anhydrous organic solvent and the mixture was incubated at a predetermined temperature in an orbital air-bath shaker (200 rpm). Aliquots were withdrawn at specified time intervals from the reaction mixture and then diluted 50-fold with corresponding mobile phase priorto HPLC analysis. Regioselectivity was defined as the molar ratio of the desired product to the total amount of ester products formed. All data are averages of experiments performed in triplicate.
  • 84
  • [ 2146-71-6 ]
  • [ 54-25-1 ]
  • 6-azauridine 5'-laurate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 4h; Enzymatic reaction; regioselective reaction; Enzymatic acylation of nucleoside General procedure: In a typical experiment, 6-azauridine (0.04 mmol), C. antarctica lipase B and vinyl ester were added into 2 mL anhydrous organic solvent and the mixture was incubated at a predetermined temperature in an orbital air-bath shaker (200 rpm). Aliquots were withdrawn at specified time intervals from the reaction mixture and then diluted 50-fold with corresponding mobile phase priorto HPLC analysis. Regioselectivity was defined as the molar ratio of the desired product to the total amount of ester products formed. All data are averages of experiments performed in triplicate.
  • 85
  • [ 3377-92-2 ]
  • [ 54-25-1 ]
  • 6-azauridine 5'-pivalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.1% With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 28h; Enzymatic reaction; regioselective reaction; Enzymatic acylation of nucleoside General procedure: In a typical experiment, 6-azauridine (0.04 mmol), C. antarctica lipase B and vinyl ester were added into 2 mL anhydrous organic solvent and the mixture was incubated at a predetermined temperature in an orbital air-bath shaker (200 rpm). Aliquots were withdrawn at specified time intervals from the reaction mixture and then diluted 50-fold with corresponding mobile phase priorto HPLC analysis. Regioselectivity was defined as the molar ratio of the desired product to the total amount of ester products formed. All data are averages of experiments performed in triplicate.
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