Product Name

  • Name

    L-Alanine, N-(chlorophenoxyphosphinyl)-, 1-methylethyl ester

  • EINECS
  • CAS No. 261909-49-3
  • Article Data68
  • CAS DataBase
  • Density 1.249±0.06 g/cm3 (20 oC 760 Torr)
  • Solubility (1.9 g/L) (25 oC)
  • Melting Point
  • Formula C12H17ClNO4P
  • Boiling Point 376.5±44.0 °C(Predicted)
  • Molecular Weight 305.698
  • Flash Point
  • Transport Information
  • Appearance white powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 261909-49-3 (L-Alanine, N-(chlorophenoxyphosphinyl)-, 1-methylethyl ester)
  • Hazard Symbols
  • Synonyms N-(Chlorophenoxyphosphinyl)-L-alanine 1-methylethyl ester
  • PSA 74.44000
  • LogP 3.73290

Synthetic route

O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

alanine isopropyl ester hydrochloride
39613-92-8, 62062-56-0, 62062-65-1

alanine isopropyl ester hydrochloride

phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
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
39825-33-7

isopropyl L-alanine

O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere;99%
With triethylamine In dichloromethane78%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -80℃; for 2h;
O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

(isopropoxy-2-oxo-ethyl-L-alaninyl)ammonium salt

(isopropoxy-2-oxo-ethyl-L-alaninyl)ammonium salt

phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere;80%
toluene-4-sulfonic acid; compound with 2-amino-propionic acid isopropyl ester

toluene-4-sulfonic acid; compound with 2-amino-propionic acid isopropyl ester

O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃;55%
With triethylamine In dichloromethane at -78 - 20℃;
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
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
108-95-2

phenol

phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
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
C6H12ClNO2

C6H12ClNO2

O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃;760 g
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

(S)-2-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino]propionic acid isopropyl ester
1256490-52-4

(S)-2-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino]propionic acid isopropyl ester

Conditions
ConditionsYield
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
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

1-[(2R,3R,4R,5R)-4-(benzyloxy)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione

1-[(2R,3R,4R,5R)-4-(benzyloxy)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione

(2S)-isopropyl 2-{[({(2R,3R,4R,5R)-3-(benzyloxy)-5-[2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]-4-fluoro-4-methyltetrahydrofuran-2-yl}methoxy)(phenoxy)phosphoryl]amino}propanoate

(2S)-isopropyl 2-{[({(2R,3R,4R,5R)-3-(benzyloxy)-5-[2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]-4-fluoro-4-methyltetrahydrofuran-2-yl}methoxy)(phenoxy)phosphoryl]amino}propanoate

Conditions
ConditionsYield
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%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

C22H41FN2O6Si2

C22H41FN2O6Si2

C34H57FN3O10PSi2

C34H57FN3O10PSi2

Conditions
ConditionsYield
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
261909-49-3

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
1613589-05-1

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

C24H31FN3O11P

C24H31FN3O11P

Conditions
ConditionsYield
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
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

O2',O3'-isopropylidene-1-methyl-guanosine
23392-07-6

O2',O3'-isopropylidene-1-methyl-guanosine

C26H35N6O9P

C26H35N6O9P

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In tetrahydrofuran; acetonitrile at 20℃; for 3h;91%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-chloro-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate

(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-chloro-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate

isopropyl ((((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((tert-butoxycarbonyl)oxy)-4-chloro-4-fluorotetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((tert-butoxycarbonyl)oxy)-4-chloro-4-fluorotetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
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
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

5(R)-<5-methyl-2,4(1H,3H)-pyrimidinedione>tetrahydro-3(S)-furanmethanol
146558-01-2

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
1610460-03-1

1'-(thymin-1-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In tetrahydrofuran at 25℃; for 48h; Inert atmosphere;88%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

2',3'-O-cyclopentylidene-4'-azidoinosine
926309-62-8

2',3'-O-cyclopentylidene-4'-azidoinosine

C27H33N8O9P
1170666-22-4

C27H33N8O9P

Conditions
ConditionsYield
With tert-butylmagnesium bromide In tetrahydrofuran at 20℃; for 17h;87%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

1-((1R,3S,5S)-3-(hydroxymethyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidine-2,4(1H,3H)-dione

1-((1R,3S,5S)-3-(hydroxymethyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidine-2,4(1H,3H)-dione

isopropyl((((1R,3S,5S)-1-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-oxabicyclo[3.1.0]hexan-3-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl((((1R,3S,5S)-1-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-oxabicyclo[3.1.0]hexan-3-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
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
261909-49-3

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
250698-51-2

(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate

2′-deoxy-2′,2′-difluoro-3′-O-(tert-butoxycarbonyloxy)-D-cytidine-5′-O-[phenyl(isopropoxy-L-alaninyl)]phosphate

2′-deoxy-2′,2′-difluoro-3′-O-(tert-butoxycarbonyloxy)-D-cytidine-5′-O-[phenyl(isopropoxy-L-alaninyl)]phosphate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;84%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

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
1345969-94-9

diethyl (2-amino-9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-9H-purin-6-yl)phosphonate

isopropyl ((((2R,3R,4R,5R)-5-(2-amino-6-(diethoxyphosphoryl)-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((((2R,3R,4R,5R)-5-(2-amino-6-(diethoxyphosphoryl)-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In tetrahydrofuran; acetonitrile at 20℃; for 3h;77%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

4-amino-1-((1R,3S,5S)-3-(hydroxymethyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidin-2(1H)-one

4-amino-1-((1R,3S,5S)-3-(hydroxymethyl)-2-oxabicyclo[3.1.0]hexan-1-yl)pyrimidin-2(1H)-one

C22H29N4O7P

C22H29N4O7P

Conditions
ConditionsYield
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
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

(3S,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,4,5-triyl triacetate
63597-75-1

(3S,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

(3S,4R,5S,6R)-3-acetamido-6-((((((S)-1-isopropoxy-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

(3S,4R,5S,6R)-3-acetamido-6-((((((S)-1-isopropoxy-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Conditions
ConditionsYield
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
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

C21H34N2O5Si

C21H34N2O5Si

isopropyl ((((3aS,4R,6R,6aR)-4-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyl-tetrahydrospiro[cyclopenta[d][1,3] dioxole-5,1’-cyclopropan]-6-yl)methoxy)(phenoxy)phos phoryl)-L-alaninate

isopropyl ((((3aS,4R,6R,6aR)-4-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyl-tetrahydrospiro[cyclopenta[d][1,3] dioxole-5,1’-cyclopropan]-6-yl)methoxy)(phenoxy)phos phoryl)-L-alaninate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In tetrahydrofuran at -78 - 20℃; Inert atmosphere;68%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

sodium pentafluorophenolate
2263-53-8

sodium pentafluorophenolate

(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
1334513-02-8

(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester

Conditions
ConditionsYield
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
261909-49-3

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
1609192-93-9

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
1609193-17-0

(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
ConditionsYield
With 1-methyl-1H-imidazole In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;66%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

2',3'-O,O-cyclopentylidene-4'-azidouridine
926309-54-8

2',3'-O,O-cyclopentylidene-4'-azidouridine

2-propyl N-[{1-[(3aR,4R,6R,6aS)-4-azido-tetrahydro-4-(hydroxymethyl)-2,2-cyclopentylfuro[3,4-d][1,3]dioxol-6-yl]pyrimidine-2,4(1H,3H)-dione} (phenoxy)-phosphoryl]-L-alaninate

2-propyl N-[{1-[(3aR,4R,6R,6aS)-4-azido-tetrahydro-4-(hydroxymethyl)-2,2-cyclopentylfuro[3,4-d][1,3]dioxol-6-yl]pyrimidine-2,4(1H,3H)-dione} (phenoxy)-phosphoryl]-L-alaninate

Conditions
ConditionsYield
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
261909-49-3

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
1307273-70-6

(+)-9-[(1′R,2′R,3′R,4′R)-2′-fluoro-3′-hydroxy-4′-(hydroxymethyl)-5′-methylenecyclopentan-1′-yl]-adenine

{[(1R,3R,4R)-3-(6-amino-9H-purin-9-yl)-4-fluoro-5-hydroxy-2-methylenecyclopentyl]methoxy}(phenoxyphosphoryl amino) propionic Acid Isopropyl Ester

{[(1R,3R,4R)-3-(6-amino-9H-purin-9-yl)-4-fluoro-5-hydroxy-2-methylenecyclopentyl]methoxy}(phenoxyphosphoryl amino) propionic Acid Isopropyl Ester

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In tetrahydrofuran at 0 - 20℃; Inert atmosphere;61%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

5'-(5-hexadecyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)phospho-AZT

5'-(5-hexadecyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)phospho-AZT

5'-(phosphoamidate-phospho)-AZT

5'-(phosphoamidate-phospho)-AZT

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; acetonitrile for 18h;60%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

5-(6-amino-9H-purin-9-yl)-2,2,3,3,4,4-hexafluoropentan-1-ol

5-(6-amino-9H-purin-9-yl)-2,2,3,3,4,4-hexafluoropentan-1-ol

isopropyl (((5-(6-amino-9H-purin-9-yl)-2,2,3,3,4,4-hexafluoropentyl)oxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl (((5-(6-amino-9H-purin-9-yl)-2,2,3,3,4,4-hexafluoropentyl)oxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
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
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

N'-(9-((2-hydroxyethoxy)-methyl)-6-oxo-6,9-dihydro-1H-purin-2-yl)-N,N-dimethylformimidamide
100699-59-0

N'-(9-((2-hydroxyethoxy)-methyl)-6-oxo-6,9-dihydro-1H-purin-2-yl)-N,N-dimethylformimidamide

C23H32N7O7P
1184942-68-4

C23H32N7O7P

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; Inert atmosphere;59%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

1′-cyano-2′-C-methyl-4-aza-7,9-dideazaadenosine
1191237-49-6

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
1350735-57-7

(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
ConditionsYield
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%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

C11H13N5O7

C11H13N5O7

C23H29N6O11P

C23H29N6O11P

Conditions
ConditionsYield
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
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

(3aR,4R,6S,6aS)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-fluoro-6-(hydroxymethyl)-2-methoxytetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(3aR,4R,6S,6aS)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-fluoro-6-(hydroxymethyl)-2-methoxytetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

isopropyl((((3aS,4S,6R,6aR)-6-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-cyano-4-fluoro-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl((((3aS,4S,6R,6aR)-6-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-cyano-4-fluoro-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;57%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

C22H26N8O3

C22H26N8O3

propan-2-yl (2S)-2-([phenoxy[(2R)-2-[3-[6-([[4-(piperidine-1-carbonyl)pyridin-2-yl]carbamoyl]amino)pyridin-2-yl]-4H-1,2,4-triazol-4-yl]propoxy]phosphoryl]amino)propanoate

propan-2-yl (2S)-2-([phenoxy[(2R)-2-[3-[6-([[4-(piperidine-1-carbonyl)pyridin-2-yl]carbamoyl]amino)pyridin-2-yl]-4H-1,2,4-triazol-4-yl]propoxy]phosphoryl]amino)propanoate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In N,N-dimethyl-formamide at -40 - 20℃; for 16h; Inert atmosphere;56%
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

4-((2-hydroxyethoxy)methyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

4-((2-hydroxyethoxy)methyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

isopropyl ((2-((3-carbamoyl-2-oxopyrazin-1(2H)-yl)methoxy)ethoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((2-((3-carbamoyl-2-oxopyrazin-1(2H)-yl)methoxy)ethoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
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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