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inquiryWe are Top Manufacturer of Sofosbuvir intermediate and its API. Appearance:a white to off-white colored powder Storage:store in well closed container Package:export worthy package Application:for Sofosbuvir API Transportation:non-dangerous materi
N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester(We are one of a few suppliers that can offer custom synthesis service of this product) We are specialized in custom synthesis, chemical/pharmaceutic
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inquiryProduct Description Product Name N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L- alanine 1-methylethyl ester CAS No. 1334513-02-8 Appearance White powder Assay ≥99%
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inquiryN-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester CAS No.:1334513-02-8 Name: N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester Molecular Structure: Molecu
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inquiryName:N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-Methylethyl ester CAS NO:1334513-02-8 Grade:Medical scientific research and export Molecular formula:C18H17F5NO5P Molecular weight:453.297089 Product Quality 12 years o
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inquiryN-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-Methylethyl ester Basic information Product Name: N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-Methylethyl ester
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inquiryName: Isopropyl N-[(pentafluorophenoxy)(phenoxy)phosphoryl]-L-alaninate Synonyms: (2s)-isopropyl-2-((perfluorophenoxyl)(phenoxy)phosphorylamino)Propanoate CAS:1334513-02-8 MF: C18H17F5NO5P Appearance: white powder Storage:Store in cool and dry pla
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inquiry2,3,4,5,6-pentafluorophenol
O-phenyl phosphorodichloridate
alanine isopropyl ester hydrochloride
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
sodium pentafluorophenolate
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
Stage #1: phenyl(isopropoxy-L-alaninyl) phosphorochloridate; sodium pentafluorophenolate In tetrahydrofuran at -10℃; Stage #2: With triethylamine In n-heptane; tert-butyl methyl ether pH=8; | 66.81% |
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
2,3,4,5,6-pentafluorophenol
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
alanine isopropyl ester hydrochloride
A
(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
Conditions | Yield |
---|---|
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
2,3,4,5,6-pentafluorophenol
A
(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
Conditions | Yield |
---|---|
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
A
(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
Conditions | Yield |
---|---|
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
A
(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
Conditions | Yield |
---|---|
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
O-phenyl phosphorodichloridate
alanine isopropyl ester hydrochloride
A
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
With triethylamine In n-heptane; ethyl acetate for 4 - 8h; Resolution of racemate; | 350 g |
2,3,4,5,6-pentafluorophenol
phenol
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
O-phenyl phosphorodichloridate
alanine isopropyl ester hydrochloride
A
(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
Conditions | Yield |
---|---|
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
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -5 - 20℃; for 20h; |
phenol
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Conditions | Yield |
---|---|
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
(2R,3S,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-azido-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol
Conditions | Yield |
---|---|
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 20h; Inert atmosphere; diastereoselective reaction; | 99% |
2'-deoxy-2'-fluoro-2'-methyluridine
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
sofosbuvir
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
(2R,3R,4R,5R) 5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol
Conditions | Yield |
---|---|
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 24h; Inert atmosphere; diastereoselective reaction; | 96% |
2'-deoxy-2'-fluoro-2'-methyluridine
(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
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
With dmap; N,N-dimethyl-aniline In tetrahydrofuran at 5 - 20℃; for 5h; Reagent/catalyst; Inert atmosphere; Large scale; | 93% |
5-chloropyridin-3-ol
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
lithium phenolate
Conditions | Yield |
---|---|
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
Deoxydifluorouridine
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
1-(2'-C-methyl-β-D-arabinofuranosyl)uracil
Conditions | Yield |
---|---|
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
gemcitabine
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
2'-C-methyluridine
Conditions | Yield |
---|---|
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
stavudin
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With tert-butylmagnesium chloride In tetrahydrofuran at -5 - 20℃; for 2h; Inert atmosphere; | 65% |
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