(3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine

Base Information

Chemical Name:(3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine
CAS No.:1370411-80-5
Molecular Formula:C₄₈H₆₅N₄O₉PSi
Molecular Weight:901.125
Hs Code.:

(3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine

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Chemical Property of (3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine

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Technology Process of (3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine

There total 7 articles about (3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine 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: 76.0%

: 1370411-79-2
(3'S,5'R)-1-[3'-hydroxy-5'-O-[(4,4'-dimethoxytriphenyl)-methyl]-2'-O-(tert-butyldimethyllsilyl)-3',5'-ethano-β-dribofuranosyl]thymidine

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 1370411-80-5,1415797-27-1,1415797-36-2
(3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jo300554w

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1370411-80-5,1415797-27-1,1415797-36-2
(3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine

Guidance literature:: Multi-step reaction with 4 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere

2: 20% palladium hydroxide on charcoal; hydrogen; cyclohexa-1,3-diene / ethyl acetate / 6 h / 20 °C

3: pyridine / 19 h / 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 20% palladium hydroxide on charcoal; hydrogen; cyclohexa-1,3-diene; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo300554w

Reference yield:

: 65-71-4,28806-14-6,691841-57-3
thymin

: 1370411-80-5,1415797-27-1,1415797-36-2
(3'S,5'R)-1-{3'-O-[(cyanoethoxy)(diisopropylamino)-phosphino]-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-2'-O-(tertbutyldimethyllsilyl)-3',5'-ethano-β-D-ribofuranosyl}thymidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 80 °C / Inert atmosphere

1.2: 16 h / 0 - 50 °C / Inert atmosphere

2.1: sodium methylate / methanol / 4 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere

4.1: 20% palladium hydroxide on charcoal; hydrogen; cyclohexa-1,3-diene / ethyl acetate / 6 h / 20 °C

5.1: pyridine / 19 h / 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; 20% palladium hydroxide on charcoal; hydrogen; sodium methylate; cyclohexa-1,3-diene; N-ethyl-N,N-diisopropylamine; In methanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo300554w