3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate

Base Information

Chemical Name:3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate
CAS No.:221895-89-2
Molecular Formula:C₂₇H₃₇N₄O₂₀P₃
Molecular Weight:830.527
Hs Code.:

Synonyms:3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate

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Chemical Property of 3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate

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Technology Process of 3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate

There total 4 articles about 3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 55715-03-2
4-bromomethyl-3-nitrobenzoic acid

: 221895-89-2
3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 3 h / 0 °C

2: NEt₃, DMAP / CH₂Cl₂ / 3 h

3: 54 percent / Bu₄NOH, NaI, NaOH, H₂O / CH₂Cl₂ / 17 h / 25 °C

4: 88 percent / TBAF / tetrahydrofuran / 0.25 h / 25 °C

5: 1.) 1,8-bis(dimethylamino)naphthalene, POCl₃, 2.) tributylammonium pyrophosphate, NBu₃ / 1.) trimethyl phosphate, 0 deg C, 140 min, 2.) trimethyl phosphate, DMF, 0 deg C, 5 min

With dmap; sodium hydroxide; oxalyl dichloride; tributyl-amine; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; tri(n-butyl)ammonium pyrophosphate; triethylamine; N,N-dimethyl-formamide; sodium iodide; trichlorophosphate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/(SICI)1521-3765(19990301)5:3<951::AID-CHEM951>3.0.CO;2-G

Reference yield:

: 73674-47-2
3-nitro-4-bromomethylbenzoyl chloride

: 221895-89-2
3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate

Guidance literature:: Multi-step reaction with 4 steps

1: NEt₃, DMAP / CH₂Cl₂ / 3 h

2: 54 percent / Bu₄NOH, NaI, NaOH, H₂O / CH₂Cl₂ / 17 h / 25 °C

3: 88 percent / TBAF / tetrahydrofuran / 0.25 h / 25 °C

4: 1.) 1,8-bis(dimethylamino)naphthalene, POCl₃, 2.) tributylammonium pyrophosphate, NBu₃ / 1.) trimethyl phosphate, 0 deg C, 140 min, 2.) trimethyl phosphate, DMF, 0 deg C, 5 min

With dmap; sodium hydroxide; tributyl-amine; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; tri(n-butyl)ammonium pyrophosphate; triethylamine; sodium iodide; trichlorophosphate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/(SICI)1521-3765(19990301)5:3<951::AID-CHEM951>3.0.CO;2-G

Reference yield:

: 221895-83-6
(N-allyloxycarbonyl)-5-aminopent-1-yl 4-bromomethyl-3-nitrobenzoate

: 221895-89-2
3'-O-<(4''-(N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxycarbonyl)-2''-nitrophenylmethyl>thymidine-5'-O-triphosphate

Guidance literature:: Multi-step reaction with 3 steps

1: 54 percent / Bu₄NOH, NaI, NaOH, H₂O / CH₂Cl₂ / 17 h / 25 °C

2: 88 percent / TBAF / tetrahydrofuran / 0.25 h / 25 °C

3: 1.) 1,8-bis(dimethylamino)naphthalene, POCl₃, 2.) tributylammonium pyrophosphate, NBu₃ / 1.) trimethyl phosphate, 0 deg C, 140 min, 2.) trimethyl phosphate, DMF, 0 deg C, 5 min

With sodium hydroxide; tributyl-amine; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; tri(n-butyl)ammonium pyrophosphate; sodium iodide; trichlorophosphate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/(SICI)1521-3765(19990301)5:3<951::AID-CHEM951>3.0.CO;2-G