O-phenyl phosphorodichloridate
alanine isopropyl ester hydrochloride
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With triethylamine In tert-butyl methyl ether at -65 - -50℃; for 2h; Inert atmosphere; Cooling with acetone-dry ice; | 100% |
With triethylamine In tert-butyl methyl ether at -55℃; for 2h; | 100% |
With triethylamine In dichloromethane at -78 - 20℃; for 2.5h; Inert atmosphere; | 93% |
isopropyl L-alanine
O-phenyl phosphorodichloridate
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere; | 99% |
With triethylamine In dichloromethane | 78% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at -80℃; for 2h; |
O-phenyl phosphorodichloridate
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere; | 80% |
O-phenyl phosphorodichloridate
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78 - 20℃; | 55% |
With triethylamine In dichloromethane at -78 - 20℃; |
toluene-4-sulfonic acid
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene / Heating 2: triethylamine / CH2Cl2 / -78 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: toluene / 24 h / 120 °C 2: triethylamine / dichloromethane / -78 - 20 °C View Scheme |
phenol
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate; triethylamine / dichloromethane / 2 h / -78 - 20 °C 2: triethylamine / dichloromethane / 2 h / -78 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: trichlorophosphate; triethylamine / dichloromethane / -78 - 20 °C 2: triethylamine / dichloromethane / 2 h / -78 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -78 - 20 °C 2: triethylamine / dichloromethane / 2 h / -78 - 20 °C View Scheme |
O-phenyl phosphorodichloridate
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78 - 20℃; | 760 g |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
2,3,4,5,6-pentafluorophenol
(S)-2-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 25℃; for 1h; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at -5 - 20℃; for 20.33h; Inert atmosphere; | 41% |
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
Stage #1: 1-[(2R,3R,4R,5R)-4-(benzyloxy)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione With isopropylmagnesium chloride, lithium chloride complex In tetrahydrofuran at -20℃; for 2h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at -20℃; for 4h; | 99% |
Conditions | Yield |
---|---|
Stage #1: C22H41FN2O6Si2 With isopropylmagnesium chloride In tetrahydrofuran at -25℃; for 2h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at -25 - -5℃; for 15h; Temperature; | 99% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
1-((3aR,4R,6S,6aS)-6-fluoro-6-(hydroxymethyl)-2-methoxy-3a-methyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4-(1H,3H)-dione
Conditions | Yield |
---|---|
Stage #1: 1-((3aR,4R,6S,6aS)-6-fluoro-6-(hydroxymethyl)-2-methoxy-3a-methyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4-(1H,3H)-dione With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 20℃; | 93% |
Stage #1: 1-((3aR,4R,6S,6aS)-6-fluoro-6-(hydroxymethyl)-2-methoxy-3a-methyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4-(1H,3H)-dione With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 0 - 20℃; | 93% |
Stage #1: 1-((3aR,4R,6S,6aS)-6-fluoro-6-(hydroxymethyl)-2-methoxy-3a-methyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4-(1H,3H)-dione With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 20℃; | 93% |
Stage #1: 1-((3aR,4R,6S,6aS)-6-fluoro-6-(hydroxymethyl)-2-methoxy-3a-methyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4-(1H,3H)-dione With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 20℃; | 93% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
O2',O3'-isopropylidene-1-methyl-guanosine
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In tetrahydrofuran; acetonitrile at 20℃; for 3h; | 91% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 1h; | 89% |
Stage #1: (2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-chloro-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate With tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 20℃; for 1h; | 89% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
5(R)-<5-methyl-2,4(1H,3H)-pyrimidinedione>tetrahydro-3(S)-furanmethanol
1'-(thymin-1-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In tetrahydrofuran at 25℃; for 48h; Inert atmosphere; | 88% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
2',3'-O-cyclopentylidene-4'-azidoinosine
C27H33N8O9P
Conditions | Yield |
---|---|
With tert-butylmagnesium bromide In tetrahydrofuran at 20℃; for 17h; | 87% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
Stage #1: 1-((1R,3S,5S)-3-(hydroxymethyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidine-2,4(1H,3H)-dione With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran for 2h; Inert atmosphere; | 85% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate
Conditions | Yield |
---|---|
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | 84% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
diethyl (2-amino-9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-9H-purin-6-yl)phosphonate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In tetrahydrofuran; acetonitrile at 20℃; for 3h; | 77% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
Stage #1: 4-amino-1-((1R,3S,5S)-3-(hydroxymethyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidin-2(1H)-one With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran Inert atmosphere; | 72% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
(3S,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,4,5-triyl triacetate
Conditions | Yield |
---|---|
Stage #1: (3S,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,4,5-triyl triacetate With tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; | 68% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 68% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
sodium pentafluorophenolate
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
Stage #1: phenyl(isopropoxy-L-alaninyl) phosphorochloridate; sodium pentafluorophenolate In tetrahydrofuran at -10℃; Stage #2: With triethylamine In n-heptane; tert-butyl methyl ether pH=8; | 66.81% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
4-((benzyloxy)amino)-1-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one
(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(4-((benzyloxy)amino)-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | 66% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
2',3'-O,O-cyclopentylidene-4'-azidouridine
Conditions | Yield |
---|---|
Stage #1: 2',3'-O,O-cyclopentylidene-4'-azidouridine With tert-butylmagnesium chloride In tetrahydrofuran for 0.25h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran for 17h; Further stages.; | 64% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
(+)-9-[(1′R,2′R,3′R,4′R)-2′-fluoro-3′-hydroxy-4′-(hydroxymethyl)-5′-methylenecyclopentan-1′-yl]-adenine
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 61% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; acetonitrile for 18h; | 60% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
Stage #1: 5-(6-amino-9H-purin-9-yl)-2,2,3,3,4,4-hexafluoropentan-1-ol With 1-methyl-1H-imidazole In tetrahydrofuran at 0℃; for 0.25h; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 20℃; for 2h; | 60% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
N'-(9-((2-hydroxyethoxy)-methyl)-6-oxo-6,9-dihydro-1H-purin-2-yl)-N,N-dimethylformimidamide
C23H32N7O7P
Conditions | Yield |
---|---|
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; Inert atmosphere; | 59% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
1′-cyano-2′-C-methyl-4-aza-7,9-dideazaadenosine
(2S)-isopropyl 2-((((2R,3R,4R,5R)-5-(4-aminopyrrolo[1,2-f]-[1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; trimethyl phosphite In tetrahydrofuran at 0 - 20℃; for 1.5h; | 59% |
With 1-methyl-1H-imidazole; trimethyl phosphite In tetrahydrofuran at 0 - 20℃; for 1.5h; | 59% |
With 1-methyl-1H-imidazole; trimethyl phosphite In tetrahydrofuran at 0 - 25℃; for 1.5h; | 59% |
Conditions | Yield |
---|---|
Stage #1: C11H13N5O7 With tert-butylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere; | 58% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere; | 57% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
With tert-butylmagnesium chloride In N,N-dimethyl-formamide at -40 - 20℃; for 16h; Inert atmosphere; | 56% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
Conditions | Yield |
---|---|
Stage #1: 4-((2-hydroxyethoxy)methyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide With pyridine; 1-methyl-1H-imidazole In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 20℃; Inert atmosphere; | 55% |
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