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261909-49-3

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  • L-Alanine, N-(chlorophenoxyphosphinyl)-, 1-Methylethyl ester/ CAS:261909-49-3/ raw material/ high-quality

    Cas No: 261909-49-3

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261909-49-3 Usage

General Description

L-Alanine, N-(chlorophenoxyphosphinyl)-, 1-methylethyl ester is a chemical compound that is a derivative of L-alanine, which is a non-essential amino acid. The compound also contains a chlorophenoxyphosphinyl group and an isopropyl ester group. This chemical may be used in organic synthesis and as a reagent in chemical reactions. It may also have potential applications in the development of pharmaceuticals or other bioactive compounds. It is important to handle and use this compound with caution, following proper safety protocols and handling procedures.

Check Digit Verification of cas no

The CAS Registry Mumber 261909-49-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,6,1,9,0 and 9 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 261909-49:
(8*2)+(7*6)+(6*1)+(5*9)+(4*0)+(3*9)+(2*4)+(1*9)=153
153 % 10 = 3
So 261909-49-3 is a valid CAS Registry Number.

261909-49-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name isopropyl N-[chloro(phenoxy)phosphoryl]-L-alaninate

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:261909-49-3 SDS

261909-49-3Synthetic 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%

261909-49-3Downstream Products

261909-49-3Relevant articles and documents

Synthesis of 2′-deoxy-2′-fluoro-2′-C-methyl spiro cyclopentyl carbocyclic uridine analog as potential inhibitors of HCV NS5B polymerase

Chu, Chung K.,Singh, Uma S.

, p. 52 - 68 (2020)

Synthesis of 1-((4 R,5S,6R,7R)-5,6-dihydroxy-7-(hydroxymethyl)spiro[2.4]heptan-4-yl)pyrimidine-2,4(1H,3H)-dione (12) and its phosphoramidate prodrug 18 is reported. The synthesis of the targeted compound 12 was initiated from triol 1. By the introduction of a substituent methylene group at 6-position of 4, followed by Simmons-Smith cyclopropanation and amination, key intermediate 10 was synthesized. The intermediate amine 10 was utilized to synthesize the nucleoside 12. Furthermore, the nucleoside 12 was derivatized to 2′-α-hydroxy-2′-β-methyl (23) and 2′-α-fluoro-2′-β-methyl (27) analogs. All synthesized derivatives of spiro-cyclopropyl carbocyclic uridine analogs 12, 18, 23 and 27 were evaluated for anti-HCV activity, but none of the compounds, reported in this article show any anti-HCV activity.

Synthesis of an Anti-hepatitis B Agent, 2′-Fluoro-6′-methylene-carbocyclic Adenosine (FMCA) and Its Phosphoramidate (FMCAP)

Singh, Uma S.,Mulamoottil, Varughese A.,Chu, Chung K.

, p. 752 - 759 (2019)

2′-Fluoro-6′-methylene-carbocyclic adenosine (FMCA, 12) and its phosphoramidate prodrug (FMCAP, 14) have been proven as a potential anti-HBV agent against both adefovir-resistant as well as lamivudine-resistant double (rtL180M/rtM204V) mutants. Furthermore, in vitro, these agents have demonstrated significant activity against lamivudine/entecavir triple mutants (L180M + S202G + M204V). These preliminary results encourage us for further biological evaluation of FMCA and FMCAP to develop as a potential clinical candidate as an anti-HBV agent, which may overcome the problem of drug resistance in HBV therapy. To support the preclinical exploration, a scalable synthesis of this molecule was needed. In this communication, a practical and scalable synthesis of FMCA, and its prodrug, is reported via ketone 1. The selective opening of the isopropylidene group of 2 led to compound 3. Protection of the allylic hydroxyl group of 3, followed by fluorination and deprotection, afforded the key intermediate 10, which was condensed with a Boc-protected adenine, followed by deprotection, furnished the target nucleoside FMCA (12) in high yield. Further coupling of phosphorochloridate of L-alanine isopropyl ester (13) with FMCA gave its phosphoramidate prodrug FMCAP (14) in good yield.

Polycyclic pyridinone compounds and pharmaceutical compositions and uses thereof

-

Paragraph 0171-0175, (2021/11/06)

The invention discloses a polycyclic pyridone compound as well as a pharmaceutical composition and application thereof, and the polycyclic pyridone compound is shown as a formula (I). The compound can be used for preparing anti-virus infection drugs.

Compound containing guanidyl group, and preparation method and application thereof

-

Paragraph 0122-0126; 0130-0132, (2021/08/07)

The invention provides a preparation containing a guanidino compound and used for treating pneumoviridae virus infection, a method, a compound of a formula I, and a method and an intermediate for synthesizing the compound of the formula I.

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