1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil

Base Information

Chemical Name:1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil
CAS No.:1363739-56-3
Molecular Formula:C₂₆H₄₀FN₂O₇PSi
Molecular Weight:570.67
Hs Code.:

Synonyms:1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil

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Chemical Property of 1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil

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Technology Process of 1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil

There total 5 articles about 1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil 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: 84.0%

: 1363739-50-7
1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-bromouracil

: 1765-93-1
4-fluoroboronic acid

: 1363739-56-3
1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In water; N,N-dimethyl-formamide; at 130 ℃; for 6h; Inert atmosphere;
DOI:10.1080/15257770.2012.654876

Reference yield:

: 1363739-44-9
1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hex-5-enofuranosyl]uracil

: 1363739-56-3
1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil

Guidance literature:: Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / methanol

2: N-Bromosuccinimide / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; N,N-dimethyl-formamide / 6 h / 130 °C / Inert atmosphere

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; sodium carbonate; In methanol; water; N,N-dimethyl-formamide; 3: Suzuki-Miyaura coupling;
DOI:10.1080/15257770.2012.654876

Reference yield:

: 76223-05-7
1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

: 1363739-56-3
1-[3-O-tert-butyldimethylsilyl-2,5,6-trideoxy-6-(diethoxyphosphinyl)-β-D-hexofuranosyl]-5-(4-fluorophenyl)uracil

Guidance literature:: Multi-step reaction with 5 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 6 h / 80 °C

2: dimethyl sulfoxide / 20 h

3: palladium 10% on activated carbon; hydrogen / methanol

4: N-Bromosuccinimide / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; N,N-dimethyl-formamide / 6 h / 130 °C / Inert atmosphere

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; sodium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 2: Wittig reaction / 5: Suzuki-Miyaura coupling;
DOI:10.1080/15257770.2012.654876