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5-Hydroxy-uridin
2-(triphenylphosphoranylidene)acetamide
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
In 1,4-dioxane Heating; | 99% |
2-thio-5-<(methylcarboxy)methyl>uridine
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 25℃; for 18h; Substitution; | 75% |
5-<(methylcarboxy)methyl>uridine
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
With ammonium hydroxide Ambient temperature; | 61.6% |
With ammonia In methanol for 48h; | |
With ammonia In methanol for 48h; | |
With ammonia In methanol at 20℃; for 48h; | |
With ammonium hydroxide In methanol at 20℃; |
uridine
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: pyridine / 3 h / 60 °C 2: acetic anhydride; acetic acid; bromine / 0 - 20 °C 3: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 5: sodium methylate / methanol / 16 h / 50 °C 6: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 6 steps 1: pyridine / 3 h / 60 °C 2: bromine; acetic anhydride; acetic acid / 0 - 20 °C / Sealed tube 3: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 5: sodium methylate; methanol / 16 h / 50 °C 6: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 6 steps 1: pyridine / 3 h / 60 °C 2: bromine; acetic anhydride / acetic acid / 0 - 20 °C / Sealed tube 3: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 5: sodium methylate / methanol / 16 h / 50 °C 6: ammonia / methanol / 48 h / 20 °C View Scheme |
Tri-O-acetyluridine
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: acetic anhydride; acetic acid; bromine / 0 - 20 °C 2: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 4: sodium methylate / methanol / 16 h / 50 °C 5: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 5 steps 1: bromine; acetic anhydride; acetic acid / 0 - 20 °C / Sealed tube 2: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 4: sodium methylate; methanol / 16 h / 50 °C 5: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 5 steps 1: bromine; acetic anhydride / acetic acid / 0 - 20 °C / Sealed tube 2: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 4: sodium methylate / methanol / 16 h / 50 °C 5: ammonia / methanol / 48 h / 20 °C View Scheme |
5-bromo-2’,3’,5’-tri-O-acetyluridine
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 3: sodium methylate / methanol / 16 h / 50 °C 4: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 0.5 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 3: sodium methylate; methanol / 16 h / 50 °C 4: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 3: sodium methylate / methanol / 16 h / 50 °C 4: ammonia / methanol / 48 h / 20 °C View Scheme |
5-bromo-N3-benzoyl-2’,3’,5’-tri-O-acetyluridine
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 2: sodium methylate / methanol / 16 h / 50 °C 3: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 2: sodium methylate; methanol / 16 h / 50 °C 3: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C 2: sodium methylate / methanol / 16 h / 50 °C 3: ammonia / methanol / 48 h / 20 °C View Scheme |
N3-benzoyl-2',3',5'-O-triacetoxyuridine-5-malonic acid dimethyl ester
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 16 h / 50 °C 2: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 2 steps 1: sodium methylate; methanol / 16 h / 50 °C 2: ammonia / methanol / 48 h View Scheme | |
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 16 h / 50 °C 2: ammonia / methanol / 48 h / 20 °C View Scheme |
triethylamine carbonate
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Stage #1: 5-(carbamoylmethyl)uridine 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; | 10.52% |
triethylamine carbonate
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Stage #1: 5-(carbamoylmethyl)uridine 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; | 10.52% |
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Stage #1: 5-(carbamoylmethyl)uridine With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere; |
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 0.17 h / 0 °C 1.2: 2 h / Inert atmosphere 2.1: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / acetonitrile / 0.42 h View Scheme |
5-(carbamoylmethyl)uridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 0.17 h / 0 °C 1.2: 2 h / Inert atmosphere 2.1: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / acetonitrile / 0.42 h 3.1: aq. buffer / 1 h / 20 °C View Scheme |
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