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Sofosbuvir intermediate
Cas No: 1334513-02-8
No Data 1 Kilogram 200 Kilogram/Month Hangzhou Maytime Bio-Tech Co.,Ltd. Contact Supplier
N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester
Cas No: 1334513-02-8
USD $ 23.0-23.0 / Gram 1 Gram 200 Metric Ton/Year Jinan Finer Chemical Co., Ltd Contact Supplier
N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester
Cas No: 1334513-02-8
USD $ 100.0-100.0 / Metric Ton 1 Metric Ton 1-100 Metric Ton/Day Shandong Jucheng Import & Export Co. , Ltd. Contact Supplier
N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester
Cas No: 1334513-02-8
USD $ 2000.0-2500.0 / Gram 100 Gram 100 Kilogram/Month ACHIEVER SYSTEAM BIOCHEM CO., LTD. Contact Supplier
N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester
Cas No: 1334513-02-8
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
(S)-Isopropyl 2-(((S)-(perfluorophenoxy)-(phenoxy)-phosphoryl)-amino)-propanoate
Cas No: 1334513-02-8
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
High Quality 99% 1334513-02-8 Isopropyl N-[(pentafluorophenoxy)(phenoxy)phosphoryl]-L-alaninate Manufacturer
Cas No: 1334513-02-8
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
1334513-02-8 N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-Methylethyl ester
Cas No: 1334513-02-8
No Data 1 Kilogram 20 Metric Ton/Day Henan Allgreen Chemical Co.,Ltd Contact Supplier
Factory Supply Propan-2-yl N-[(S)-(pentafluorophenoxy)(phenoxy) phosphoryl]-L-alaninate
Cas No: 1334513-02-8
No Data 1 1 Ality Chemical Corporation Contact Supplier
N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester
Cas No: 1334513-02-8
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier

1334513-02-8 Usage

InChI:InChI=1S/C18H17F5NO5P/c1-9(2)27-18(25)10(3)24-30(26,28-11-7-5-4-6-8-11)29-17-15(22)13(20)12(19)14(21)16(17)23/h4-10H,1-3H3,(H,24,26)/t10-,30?/m0/s1

1334513-02-8SDS

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 propan-2-yl (2S)-2-[[(2,3,4,5,6-pentafluorophenoxy)-phenoxyphosphoryl]amino]propanoate

1.2 Other means of identification

Product number -
Other names N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine1-Methylethylester

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:1334513-02-8 SDS

1334513-02-8Synthetic route

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

2,3,4,5,6-pentafluorophenol

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

(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: 2,3,4,5,6-pentafluorophenol; O-phenyl phosphorodichloridate With triethylamine In chloroform at 0℃; under 11251.1 Torr;
Stage #2: alanine isopropyl ester hydrochloride In chloroform Temperature;
88%
Stage #1: alanine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at -68℃; for 0.5h;
Stage #2: O-phenyl phosphorodichloridate In dichloromethane at -10℃; for 0.5h;
Stage #3: 2,3,4,5,6-pentafluorophenol With N-ethyl-N,N-diisopropylamine In dichloromethane
78%
Stage #1: O-phenyl phosphorodichloridate; alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -78 - 20℃; for 2h;
Stage #2: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at -78 - 20℃; for 3h;
61.6%
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

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

2,3,4,5,6-pentafluorophenol

(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
With triethylamine In dichloromethane at 0℃; for 4h;45.1%
With triethylamine In dichloromethane at 0℃; for 4h; Inert atmosphere;45.1%
2,3,4,5,6-pentafluorophenyl dichlorophosphate
17788-07-7

2,3,4,5,6-pentafluorophenyl dichlorophosphate

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

alanine isopropyl ester hydrochloride

A

(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

B

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
1337529-56-2

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: 2,3,4,5,6-pentafluorophenyl dichlorophosphate With triethylamine; phenol In dichloromethane at 20℃; for 0.5h;
Stage #2: alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at 0℃; for 1h;
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

A

(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

B

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
1337529-56-2

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
With triethylamine In dichloromethane at -10 - 0℃; for 1.5h;A n/a
B n/a
With triethylamine In dichloromethane at -15 - 5℃; for 1h; Inert atmosphere;A n/a
B n/a
alanine isopropyl ester hydrochloride
39613-92-8, 62062-56-0, 62062-65-1

alanine isopropyl ester hydrochloride

A

(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

B

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
1337529-56-2

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 0.5 h / -10 °C / Inert atmosphere
2: triethylamine / dichloromethane / 1.5 h / -10 - 0 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / tert-butyl methyl ether / 2 h / -65 - -50 °C / Inert atmosphere; Cooling with acetone-dry ice
2: triethylamine / dichloromethane / 1 h / -15 - 5 °C / Inert atmosphere
View Scheme
O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

A

(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

B

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
1337529-56-2

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 0.5 h / -10 °C / Inert atmosphere
2: triethylamine / dichloromethane / 1.5 h / -10 - 0 °C
View Scheme
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

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

A

(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

B

C18H17F5NO4P

C18H17F5NO4P

Conditions
ConditionsYield
Stage #1: alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -70℃; for 0.75h;
Stage #2: O-phenyl phosphorodichloridate In dichloromethane at -70 - 0℃; for 8h;
Stage #3: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at 0 - 20℃;
O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

(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
Multi-step reaction with 2 steps
1.1: triethylamine / ethyl acetate / 1 h / -10 °C / Enzymatic reaction
1.2: 2.5 h / -5 - 25 °C
2.1: triethylamine / ethyl acetate; n-heptane / 4 - 8 h / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 1.5 h / -60 - 25 °C / Inert atmosphere
2.1: tetrahydrofuran / -10 °C
2.2: pH 8
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 20 h / -70 - 20 °C
2: triethylamine / dichloromethane / 20 h / -5 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 1 h / -78 - 20 °C
2: triethylamine / dichloromethane / 4 h / 0 °C
View Scheme
isopropyl L-alanine
39825-33-7

isopropyl L-alanine

(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
Multi-step reaction with 2 steps
1.1: triethylamine / ethyl acetate / 1 h / -10 °C / Enzymatic reaction
1.2: 2.5 h / -5 - 25 °C
2.1: triethylamine / ethyl acetate; n-heptane / 4 - 8 h / Resolution of racemate
View Scheme
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

(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
Multi-step reaction with 2 steps
1.1: triethylamine / ethyl acetate / 1 h / -10 °C / Enzymatic reaction
1.2: 2.5 h / -5 - 25 °C
2.1: triethylamine / ethyl acetate; n-heptane / 4 - 8 h / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 25 - 30 °C
2.1: tetrahydrofuran / -10 °C
2.2: pH 8
View Scheme
(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

(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
With triethylamine In n-heptane; ethyl acetate for 4 - 8h; Resolution of racemate;350 g
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

N-dichlorophosphoryl-L-alanine isopropyl ester

N-dichlorophosphoryl-L-alanine isopropyl ester

phenol
108-95-2

phenol

(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: N-dichlorophosphoryl-L-alanine isopropyl ester; phenol With triethylamine In dichloromethane at 0 - 20℃; for 1h;
Stage #2: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at 20℃; for 5h; Reagent/catalyst; Cooling with ice;
10.8 g
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

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

A

(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

B

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
1337529-56-2

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: O-phenyl phosphorodichloridate; alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -60℃; Inert atmosphere; Green chemistry;
Stage #2: 2,3,4,5,6-pentafluorophenol In dichloromethane at 20℃; for 3h; Inert atmosphere; Green chemistry;
Stage #1: O-phenyl phosphorodichloridate; alanine isopropyl ester hydrochloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With triethylamine In dichloromethane at -60℃; Inert atmosphere;
Stage #3: 2,3,4,5,6-pentafluorophenol In dichloromethane at 0 - 5℃; for 4h; Inert atmosphere;
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

C12H17ClNO4P

C12H17ClNO4P

(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
With triethylamine In dichloromethane at -5 - 20℃; for 20h;
phenol
108-95-2

phenol

(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
Multi-step reaction with 3 steps
1: trichlorophosphate; triethylamine / diethyl ether / -78 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 1 h / -78 - 20 °C
3: triethylamine / dichloromethane / 4 h / 0 °C
View Scheme
(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

(2R,3S,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-azido-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol
1403249-88-6

(2R,3S,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-azido-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

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

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

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 20h; Inert atmosphere; diastereoselective reaction;99%
2'-deoxy-2'-fluoro-2'-methyluridine
863329-66-2

2'-deoxy-2'-fluoro-2'-methyluridine

(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

sofosbuvir
1190307-88-0

sofosbuvir

Conditions
ConditionsYield
With pyridine; aluminum (III) chloride In dichloromethane at 20℃; Reagent/catalyst; Temperature;97.5%
With 2,6-dimethylpyridine; dimethylaluminum chloride In tetrahydrofuran; hexane at 0 - 45℃; for 20h;86%
Stage #1: 2'-deoxy-2'-fluoro-2'-methyluridine With 3,3-diphenyl-2-propenal; tert-butylmagnesium chloride In tetrahydrofuran at -5 - 5℃; for 19h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran Reagent/catalyst;
86.2%
(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

2',3'-isopropylidene adenosine
362-75-4

2',3'-isopropylidene adenosine

(S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(6-amino-0H-purin-9-yl)-2,2-dimethyltetrahydrofuro-[3,4-d]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propionoate
1334513-09-5

(S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(6-amino-0H-purin-9-yl)-2,2-dimethyltetrahydrofuro-[3,4-d]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propionoate

Conditions
ConditionsYield
Stage #1: 2',3'-isopropylidene adenosine With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.55h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 20℃; for 18.05h;
96%
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 6h; Inert atmosphere; diastereoselective reaction;94%
(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

(2R,3R,4R,5R) 5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol
1199809-30-7

(2R,3R,4R,5R) 5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

isopropyl ((S)-(((2R,3R,4R,5R)-5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((S)-(((2R,3R,4R,5R)-5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 24h; Inert atmosphere; diastereoselective reaction;96%
2'-deoxy-2'-fluoro-2'-methyluridine
863329-66-2

2'-deoxy-2'-fluoro-2'-methyluridine

(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

(S)-2-{(R)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid isopropyl ester
1190308-01-0

(S)-2-{(R)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: 2'-deoxy-2'-fluoro-2'-methyluridine With isopropyl magnesium chloride lithium chloride complex In tetrahydrofuran at -60℃; for 1h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at -50℃; for 1h; Temperature; Reagent/catalyst;
95%
Stage #1: 2'-deoxy-2'-fluoro-2'-methyluridine With tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 1.16667h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 5 - 20℃; for 10h; Inert atmosphere;
76%
(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

C11H15FN2O4

C11H15FN2O4

(S)-2-{(R)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid isopropyl ester
1190308-01-0

(S)-2-{(R)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid isopropyl ester

Conditions
ConditionsYield
With dmap; N,N-dimethyl-aniline In tetrahydrofuran at 5 - 20℃; for 5h; Reagent/catalyst; Inert atmosphere; Large scale;93%
5-chloropyridin-3-ol
74115-12-1

5-chloropyridin-3-ol

(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

lithium phenolate
555-24-8

lithium phenolate

C17H20ClN2O5P

C17H20ClN2O5P

Conditions
ConditionsYield
With lithium tert-butoxide In tetrahydrofuran at 0 - 10℃; for 2h; Reagent/catalyst; Temperature; Large scale;92%
(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

Deoxydifluorouridine
114248-23-6

Deoxydifluorouridine

isopropyl ((S)-(((2R,3R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((S)-(((2R,3R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 20h; Inert atmosphere; diastereoselective reaction;87%
Stage #1: Deoxydifluorouridine With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 1.5h;
(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

(+)-2-((2S,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile

(+)-2-((2S,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile

(+)-isopropyl ((S)-(((2S,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3-(cyanomethyl)-4-fluoro-3-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

(+)-isopropyl ((S)-(((2S,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3-(cyanomethyl)-4-fluoro-3-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
Stage #1: (+)-2-((2S,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile With tert-butylmagnesium bromide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran for 16h; Inert atmosphere;
87%
(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

C15H19N3O6

C15H19N3O6

C27H35N4O10P

C27H35N4O10P

Conditions
ConditionsYield
With 2,6-dimethylpyridine; aluminum tri-tert-butoxide In tetrahydrofuran at 20℃; for 15h;86%
(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

1-(2'-C-methyl-β-D-arabinofuranosyl)uracil
114262-49-6

1-(2'-C-methyl-β-D-arabinofuranosyl)uracil

(S)-isopropyl 2-(((S)-(((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-di-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino) propanoate

(S)-isopropyl 2-(((S)-(((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-di-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino) propanoate

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 50℃; for 25h; Inert atmosphere; diastereoselective reaction;86%
(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

gemcitabine
95058-81-4

gemcitabine

isopropyl ((S)-(((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((S)-(((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 22h; Inert atmosphere; diastereoselective reaction;83%
(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

1‐((2R,3R,4R,5R)‐3‐fluoro‐4‐hydroxy‐5‐(hydroxy‐[D2]methyl)‐3‐methyltetrahydrofuran‐2‐yl)pyrimidine‐2,4(1H,3H)‐dione

1‐((2R,3R,4R,5R)‐3‐fluoro‐4‐hydroxy‐5‐(hydroxy‐[D2]methyl)‐3‐methyltetrahydrofuran‐2‐yl)pyrimidine‐2,4(1H,3H)‐dione

isopropyl ((S)‐(((2R,3R,4R,5R)‐5‐(2,4‐dioxo‐3,4‐dihydropyrimidin‐1(2H)‐yl)‐4‐fluoro‐3‐hydroxy‐4‐methyltetrahydrofuran‐2‐yl) [D2]methoxy)(phenoxy)phosphoryl)‐L‐alaninate

isopropyl ((S)‐(((2R,3R,4R,5R)‐5‐(2,4‐dioxo‐3,4‐dihydropyrimidin‐1(2H)‐yl)‐4‐fluoro‐3‐hydroxy‐4‐methyltetrahydrofuran‐2‐yl) [D2]methoxy)(phenoxy)phosphoryl)‐L‐alaninate

Conditions
ConditionsYield
Stage #1: 1‐((2R,3R,4R,5R)‐3‐fluoro‐4‐hydroxy‐5‐(hydroxy‐[D2]methyl)‐3‐methyltetrahydrofuran‐2‐yl)pyrimidine‐2,4(1H,3H)‐dione With tert-butylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 16h;
82%
Stage #1: 1‐((2R,3R,4R,5R)‐3‐fluoro‐4‐hydroxy‐5‐(hydroxy‐[D2]methyl)‐3‐methyltetrahydrofuran‐2‐yl)pyrimidine‐2,4(1H,3H)‐dione With tert-butylmagnesium chloride In tetrahydrofuran at -5 - 20℃;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 5℃;
40%
With tert-butylmagnesium chloride In tetrahydrofuran
(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

[(1SR,2SR,4RS)-4-(2-amino-6-ethoxy-9H-purin-9-yl)-1-ethynyl-2-(methoxymethoxy)cyclopentyl]methanol

[(1SR,2SR,4RS)-4-(2-amino-6-ethoxy-9H-purin-9-yl)-1-ethynyl-2-(methoxymethoxy)cyclopentyl]methanol

propan-2-yl N-[(S)-{[(1RS,2RS,4SR)-4-(2-amino-6-ethoxy-9H-purin-9-yl)-1-ethynyl-2-(methoxymethoxy)cyclopentyl]methoxy}(phenoxy)phosphoryl]-L-alaninate

propan-2-yl N-[(S)-{[(1RS,2RS,4SR)-4-(2-amino-6-ethoxy-9H-purin-9-yl)-1-ethynyl-2-(methoxymethoxy)cyclopentyl]methoxy}(phenoxy)phosphoryl]-L-alaninate

Conditions
ConditionsYield
Stage #1: [(1SR,2SR,4RS)-4-(2-amino-6-ethoxy-9H-purin-9-yl)-1-ethynyl-2-(methoxymethoxy)cyclopentyl]methanol With tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;
82%
(2R,3R,4R,5R) 5-(2-amino-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol
1199809-27-2

(2R,3R,4R,5R) 5-(2-amino-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

(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

(S)-2-{(S)-[(1R,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-4-(R)-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-ylmethoxy]phenoxy-phosphorylamino}propionic acid isopropyl ester
1231747-08-2

(S)-2-{(S)-[(1R,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-4-(R)-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-ylmethoxy]phenoxy-phosphorylamino}propionic acid isopropyl ester

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 16h; Inert atmosphere; diastereoselective reaction;81%
(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

1-((2R,3R,4R,5R)-3-bromo-3-chloro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4( 1H,3H)-dione

1-((2R,3R,4R,5R)-3-bromo-3-chloro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4( 1H,3H)-dione

(S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-4-bromo-4-chloro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-4-bromo-4-chloro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Stage #1: 1-((2R,3R,4R,5R)-3-bromo-3-chloro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4( 1H,3H)-dione With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 1.5h;
81%
(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

(+)-2-((2S,3R,4S,5R)-5-(2-chloro-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile

(+)-2-((2S,3R,4S,5R)-5-(2-chloro-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile

(+)-isopropyl ((S)-(((2S,3R,4S,5R)-5-(2-chloro-6-methoxy-9H-purin-9-yl)-3-(cyanomethyl)-4-fluoro-3-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

(+)-isopropyl ((S)-(((2S,3R,4S,5R)-5-(2-chloro-6-methoxy-9H-purin-9-yl)-3-(cyanomethyl)-4-fluoro-3-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
Stage #1: (+)-2-((2S,3R,4S,5R)-5-(2-chloro-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile With tert-butylmagnesium bromide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran for 16h; Inert atmosphere;
80%
(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

2'-C-methyluridine
31448-54-1

2'-C-methyluridine

isopropyl ((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 50℃; for 25h; Inert atmosphere; diastereoselective reaction;79%
Stage #1: 2'-C-methyluridine With tert-butylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 20℃;
56%
Stage #1: 2'-C-methyluridine With tert-butylmagnesium chloride In tetrahydrofuran at -5 - 20℃; for 1.5h; Inert atmosphere; Schlenk technique;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 20℃; for 17h; Inert atmosphere;
24%
(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

stavudin
3056-17-5

stavudin

isopropyl ((S)-(((2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((S)-(((2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 20h; Inert atmosphere; diastereoselective reaction;78%
(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

(+)-2-((2S,3R,4S,5R)-5-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile

(+)-2-((2S,3R,4S,5R)-5-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile

(+)-isopropyl ((S)-(((2S,3R,4S,5R)-5-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-3-(cyanomethyl)-4-fluoro-3-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

(+)-isopropyl ((S)-(((2S,3R,4S,5R)-5-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-3-(cyanomethyl)-4-fluoro-3-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
Stage #1: (+)-2-((2S,3R,4S,5R)-5-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)acetonitrile With tert-butylmagnesium bromide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran for 16h; Inert atmosphere;
76%
(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

2',3'-isopropylideneguanosine
362-76-5

2',3'-isopropylideneguanosine

(S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1334513-11-9

(S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Stage #1: 2',3'-isopropylideneguanosine With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.55h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 20℃; for 18.05h;
75%
(2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine
817204-33-4

(2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine

(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

(S)-isopropyl 2-(((R)-(((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1334513-10-8

(S)-isopropyl 2-(((R)-(((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With pyridine; dimethylaluminum chloride In hexane at 0 - 4℃; for 24h; Inert atmosphere; diastereoselective reaction;71%
Stage #1: (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.55h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 20℃; for 18.05h;
53%
Stage #1: (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine With tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0℃; for 1h;
30%
(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

1-((2R,3S,4R,5R)-3-chloro-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

1-((2R,3S,4R,5R)-3-chloro-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

(S)-2-(((S)-(((2R,3R,4S,5R)-4-chloro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoic acid isopropyl ester

(S)-2-(((S)-(((2R,3R,4S,5R)-4-chloro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoic acid isopropyl ester

Conditions
ConditionsYield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butylmagnesium chloride In tetrahydrofuran at -10 - -8℃; for 1.81667h; Temperature; Solvent; Reagent/catalyst; Large scale;70%
Stage #1: 1-((2R,3S,4R,5R)-3-chloro-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione With tert-butylmagnesium chloride In tetrahydrofuran; water at -10℃; for 0.666667h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; water at -10℃; for 22h;
874 mg
Stage #1: 1-((2R,3S,4R,5R)-3-chloro-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 1.5h;
(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

C18H27FN6O5

C18H27FN6O5

C30H43FN7O9P

C30H43FN7O9P

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at -10 - 20℃; for 1h;68.5%
(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

1-((2R,3S,4R,5R)-3-bromo-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4( 1H,3H)-dione

1-((2R,3S,4R,5R)-3-bromo-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4( 1H,3H)-dione

(S)-isopropyl 2-(((S)-(((2R,3R,4S,5R)-4-bromo-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(S)-isopropyl 2-(((S)-(((2R,3R,4S,5R)-4-bromo-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Stage #1: 1-((2R,3S,4R,5R)-3-bromo-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4( 1H,3H)-dione With tert-butylmagnesium chloride In tetrahydrofuran at -5 - 25℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 4℃; for 16h; Inert atmosphere;
68%
Stage #1: 1-((2R,3S,4R,5R)-3-bromo-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4( 1H,3H)-dione With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 1.5h;
62.6%
(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

C17H15(2)H2ClN2O6

C17H15(2)H2ClN2O6

C22H27(2)H2ClN3O9P

C22H27(2)H2ClN3O9P

Conditions
ConditionsYield
Stage #1: C17H15(2)H2ClN2O6 With tert-butylmagnesium chloride In tetrahydrofuran at 0 - 5℃; for 0.5h;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 5℃;
67%
(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

1-((3aR,4R,6aR)-6-((R)-1-hydroxyethyl)-2,2,3a-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione
1418141-24-8

1-((3aR,4R,6aR)-6-((R)-1-hydroxyethyl)-2,2,3a-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

isopropyl ((S)-((R)-1-((3aR,4S,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2,6a-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethoxy)(phenoxy)phosphoryl)-L-alaninate

isopropyl ((S)-((R)-1-((3aR,4S,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2,6a-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions
ConditionsYield
Stage #1: 1-((3aR,4R,6aR)-6-((R)-1-hydroxyethyl)-2,2,3a-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione With tert-butylmagnesium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at -5 - 20℃; for 1.5h; Inert atmosphere; Schlenk technique;
Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 17h; Inert atmosphere;
67%
(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

(2R,3R,4R,5R)-5-(2-amino-6-(dimethylamino)-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

(2R,3R,4R,5R)-5-(2-amino-6-(dimethylamino)-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

C25H35FN7O7P

C25H35FN7O7P

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at -5 - 20℃; for 2h; Inert atmosphere;65%

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