Welcome to LookChem.com Sign In|Join Free
  • or

1809249-37-3

Post Buying Request

1809249-37-3 Suppliers

Recommended suppliersmore

Product FOB Price Min.Order Supply Ability Supplier
Remdesivir/ LIDE PHARMA- Factory supply / Best price
Cas No: 1809249-37-3
No Data No Data 1 LIDE PHARMACEUTICALS LIMITED Contact Supplier
V Remdesivir /99% in stock
Cas No: 1809249-37-3
USD $ 10.0-10.0 / Gram 1 Gram 10 Kilogram/Day Shenzhen Tianyuan Pharmaceutical Technology Co., Ltd Contact Supplier
Remdesivir
Cas No: 1809249-37-3
No Data 100 Gram 500 Kilogram/Week Senova Technology Company Limited Contact Supplier
1809249-37-3/Remdesivir API
Cas No: 1809249-37-3
USD $ 0.1-0.1 / Gram 1 Gram hundreds of Kilogram/Month Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd Contact Supplier
Covid-19 High Purity cas 1809249-37-3 Remdesivir powder CAS NO.1809249-37-3
Cas No: 1809249-37-3
No Data 100 Gram 50 Metric Ton/Day Hebei miaobian Biotechnology Co., Ltd Contact Supplier
Remdesivir
Cas No: 1809249-37-3
No Data No Data 10 Kilogram/Month Hangzhou Maytime Bio-Tech Co.,Ltd. Contact Supplier
High Purity ,stock, Remdesivir CAS:1809249-37-3
Cas No: 1809249-37-3
No Data No Data No Data Shanghai Hope Chem Co., Ltd Contact Supplier
In stock High Purity Coronavirus Covid-19 Remdesivir powder for API
Cas No: 1809249-37-3
USD $ 11500.0-12500.0 / Kilogram 1 Kilogram 1 Metric Ton/Month Hangzhou Sartort Biopharma Co., Ltd Contact Supplier
Remdesivir (GS-5734)/ supplier with competitive price in stock-Rechems
Cas No: 1809249-37-3
No Data No Data No Data Shanghai Rechem Science Co., Ltd. Contact Supplier
Remdesivir
Cas No: 1809249-37-3
No Data No Data 10 Kilogram/Day Shanghai Innopharm Industrial Co.,Ltd Contact Supplier

1809249-37-3 Usage

Product Description:

Novel inhibitor of the replication of several taxonomically diverse RNA viruses such as Middle East respiratory syndrome virus, Ebola virus, Lassa fever virus, Junin virus and respiratory syncytial virus, while having low cytotoxicity in a wide-range of cell lines

Remdesivir Properties

Background Information

Remdesivir is a nucleoside analogue, with effective antiviral activity, with EC50s of 74 nM for ARS-CoV and MERS-CoV in HAE cells, and 30 nM for murine hepatitis virus in delayed brain tumor cells. 
Remdesivir, also known as GS-5734, is an antiviral drug, a novel nucleotide analog prodrug. It was developed by Gilead Sciences as a treatment for filovirus infections such as Ebola virus disease and Marburg virus, though it has subsequently also been found to show reasonable antiviral activity against more distantly related viruses such as respiratory syncytial virus, Junin virus, Lassa fever virus, and MERS-coronavirus. GS-5734 was rapidly pushed through clinical trials due to the 2013–2016 West African Ebola virus epidemic crisis, eventually being used in at least one human patient despite its early development stage at the time. Preliminary results have been promising, and further clinical trials are planned.
GS-5734 (Remdesivir) is a monophosphoramidate prodrug of adenosine analogue that exhibits antiviral activity against multiple variants of EBOV (EC50=70-140 nM) and other filoviruses (EC50=0.019-1.48 uM) in cell-based assays; suppresses EBOV replication and protects 100% of EBOV-infected animals against lethal disease, ameliorating clinical disease signs and pathophysiological markers.

1809249-37-3Synthetic route

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

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

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃; for 3h; pH=3 - 4; Reagent/catalyst;91%
With hydrogenchloride In tetrahydrofuran; water at 0 - 25℃; for 8h;73%
With hydrogenchloride In tetrahydrofuran; water at 20℃; Inert atmosphere;69%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C21H26N3O9P

C21H26N3O9P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Stage #1: (2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile With titanium(IV) isopropylate; tert-butylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 0.5h;
Stage #2: C21H26N3O9P In tetrahydrofuran at -10 - 20℃; Solvent; Reagent/catalyst;
86.2%
2-ethylbutyl (2S)-2-{[(S)-{[(3aR,4R,6R,6aR)-6-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-6-cyano-2-phenyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methoxy}(phenoxy)phosphoryl]amino}propanoate

2-ethylbutyl (2S)-2-{[(S)-{[(3aR,4R,6R,6aR)-6-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-6-cyano-2-phenyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methoxy}(phenoxy)phosphoryl]amino}propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
at 60℃;84%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C19H27N2O7P

C19H27N2O7P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With diisopropylamine; zinc dibromide In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere; Molecular sieve;81%
2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate
1355049-92-1

2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
1191237-80-5

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Stage #1: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile With 2,6-dimethylpyridine; C17H21N3O2 In dichloromethane at -20 - 20℃; for 0.333333h; Inert atmosphere; Molecular sieve;
Stage #2: 2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate In dichloromethane at -20 - 20℃; for 24h; Inert atmosphere; Molecular sieve;
Stage #3: With toluene-4-sulfonic acid In methanol at 20℃; for 24h; Inert atmosphere;
73%
Multi-step reaction with 2 steps
1.1: C17H21N3O2; 2,6-dimethylpyridine / dichloromethane / 0.33 h / -40 - 20 °C / Inert atmosphere; Molecular sieve
1.2: 24 h / 4 - 20 °C / Inert atmosphere; Molecular sieve
2.1: hydrogenchloride / tetrahydrofuran; water / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: C17H21N3O2; 2,6-dimethylpyridine / dichloromethane / 0.33 h / -40 - 20 °C / Inert atmosphere; Molecular sieve
1.2: 24 h / 4 - 20 °C / Inert atmosphere; Molecular sieve
2.1: hydrogenchloride / tetrahydrofuran; water / 20 °C / Inert atmosphere
View Scheme
Stage #1: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile With tert-butylmagnesium chloride In tetrahydrofuran at -40 - 30℃;
Stage #2: 2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate In tetrahydrofuran at -40 - 10℃;
100 mg
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C20H26ClN2O5P

C20H26ClN2O5P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With triethylamine; zinc(II) chloride In tetrahydrofuran at 65℃; for 25h; Inert atmosphere;44%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C20H26ClN2O5P

C20H26ClN2O5P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium chloride In 1,4-dioxane at 55℃; for 25h; Inert atmosphere;42%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C20H26BrN2O5P

C20H26BrN2O5P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With potassium carbonate; zinc dibromide In tert-butyl methyl ether at 75℃; for 25h; Inert atmosphere;40.5%
(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tert-butylmagnesium chloride / tetrahydrofuran / 16 h / -10 - 5 °C
2: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 21 h / 50 °C
2: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
(S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tertbutyldimethylsilyl)oxy)-5-cyanotetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tertbutyldimethylsilyl)oxy)-5-cyanotetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With hydrogenchloride; water at 0 - 20℃; for 72h;
(3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol
1355049-94-3

(3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
3.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
3.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
3.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
(3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy) methyl)tetrahydrofuran-2-carbonitrile
1191237-68-9

(3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy) methyl)tetrahydrofuran-2-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
2: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / acetone / 0.5 h / 45 °C
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
3: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: acetone / 0.5 h / 20 °C
2: potassium carbonate / water; ethyl acetate
3: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
4: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid / acetone / 0.5 h / 45 °C
2.1: magnesium chloride / acetonitrile / 0.25 h / 20 °C
2.2: 4 h
3.1: water; hydrogenchloride / tetrahydrofuran / 0 - 20 °C
View Scheme
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

(2S)-2-ethylbutyl 2-(((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate
1439900-56-7

(2S)-2-ethylbutyl 2-(((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

A

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

B

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
Multi-step reaction with 2 steps
1: tert-butylmagnesium chloride / N,N-dimethyl-formamide; tetrahydrofuran / 2.17 h / 20 °C / Inert atmosphere
2: Lux Cellulose-2 / acetonitrile; methanol / Resolution of racemate
View Scheme
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium chloride In N,N-dimethyl acetamide at 30℃; for 5h;
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium chloride In N,N-dimethyl acetamide at 30℃; for 6h;
4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine
1770840-43-1

4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 0.58 h / 0 - 5 °C
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 0.58 h / 0 - 5 °C
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 0.58 h / 0 - 5 °C
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
(2R,3R,4R,5R)‐2‐{4‐aminopyrrolo[2,1‐f][1,2,4]triazin‐7‐yl}‐3,4‐bis(benzyloxy)‐5‐[(benzyloxy)methyl]tetrahydrofuran‐2‐carbonitrile
1355357-49-1

(2R,3R,4R,5R)‐2‐{4‐aminopyrrolo[2,1‐f][1,2,4]triazin‐7‐yl}‐3,4‐bis(benzyloxy)‐5‐[(benzyloxy)methyl]tetrahydrofuran‐2‐carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
2: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 1.5 h / -15 °C / Inert atmosphere
1.2: 2 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 21 h / 50 °C
3.1: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
4-aminopyrrolo[2,1-f][1,2,4]triazine
159326-68-8

4-aminopyrrolo[2,1-f][1,2,4]triazine

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 0 °C
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
2.2: 0.58 h / 0 - 5 °C
3.1: trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid / dichloromethane / 0.17 h / -40 - -25 °C
4.1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 0 °C
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
2.2: 0.58 h / 0 - 5 °C
3.1: trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid / dichloromethane / 0.17 h / -40 - -25 °C
4.1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 0 °C
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
2.2: 0.58 h / 0 - 5 °C
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
2-ethylbutyl (S)-2-aminopropanoate hydrochloride
946511-97-3

2-ethylbutyl (S)-2-aminopropanoate hydrochloride

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 1.5 h / -15 °C / Inert atmosphere
1.2: 2 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 21 h / 50 °C
3.1: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one
14233-64-8, 134307-32-7, 55094-52-5

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
1.2: 0.17 h / -78 °C / Inert atmosphere
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
1.2: 0.17 h / -78 °C / Inert atmosphere
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
1.2: 0.17 h / -78 °C / Inert atmosphere
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
2: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
1191237-80-5

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
2: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium chloride / acetonitrile / 0.25 h / 20 °C
1.2: 4 h
2.1: hydrogenchloride / tetrahydrofuran; water / 0 - 20 °C
View Scheme
(3aR,4R,6R,6aR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile p-tolylsulfonic acid salt

(3aR,4R,6R,6aR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile p-tolylsulfonic acid salt

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / water; ethyl acetate
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
3: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
2,3,5-tri-O-benzyl-D-ribofuranose
16838-89-4

2,3,5-tri-O-benzyl-D-ribofuranose

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetic anhydride; dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 0.17 h / -78 °C / Inert atmosphere
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: acetic anhydride; dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 0.17 h / -78 °C / Inert atmosphere
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: acetic anhydride; dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 0.17 h / -78 °C / Inert atmosphere
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
1191237-80-5

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C
2: hydrogenchloride / tetrahydrofuran; water / 0 °C
View Scheme
With N-ethyl-N,N-diisopropylamine; magnesium chloride In tetrahydrofuran at 20℃; for 3h; Temperature;
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 50 °C / Inert atmosphere
2: hydrogenchloride / tetrahydrofuran; water / 20 °C / Inert atmosphere
View Scheme
4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine
1770840-43-1

4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine

A

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

B

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; phenylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.17 h / -15 - -12 °C
1.3: 1 h / -20 °C
2.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 °C
3.1: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.1: 1-methyl-1H-imidazole / tetrahydrofuran / 0 °C / Inert atmosphere
5.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; phenylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.17 h / -15 - -12 °C
1.3: 1 h / -20 °C
2.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 °C
3.1: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C
5.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; phenylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.17 h / -15 - -12 °C
1.3: 1 h / -20 °C
2.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 °C
3.1: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2.17 h / Inert atmosphere
5.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

A

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

B

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 4 h / -78 °C / Inert atmosphere
1.2: 4 h / 0 - 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C
3.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 4 h / -78 - 20 °C
1.2: 4 h / 0 - 20 °C
2.1: tert-butylmagnesium chloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h
3.1: Lux Cellulose-2 / acetonitrile; methanol / Resolution of racemate
View Scheme
(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

((((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)oxidophosphoryl)alanine bis-sodium salt

((((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)oxidophosphoryl)alanine bis-sodium salt

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile for 2h;

Please post your buying leads,so that our qualified suppliers will soon contact you!

*Required Fields