[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid

Base Information

• Chemical Name: [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid
• CAS No.: 179017-52-8
• Molecular Formula: C₂₇H₃₅N₂O₆PSi
• Molecular Weight: 542.644
• Mol file: 179017-52-8.mol

Synonyms:[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid

Chemical Property of [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid

There total 5 articles about [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid 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: 92.0%

[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid ethyl ester (179017-27-7,179017-28-8,195873-28-0) → [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid (179017-52-8)

Guidance literature:

With triethylamine; In ethanol; at 20 ℃;

DOI:10.1055/s-2001-12328

Reference yield:

1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine (146557-69-9) → [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid (179017-52-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / NaBH₄ / ethanol / 20 °C

2: 76 percent / MeP(+)(OPh)3I(-); 2,6-lutidine / dimethylformamide / 20 °C

3: 94 percent / KHMDS / tetrahydrofuran / -78 - 20 °C

4: 87 percent / Me₃SiCl; EtOH / CHCl₃ / 20 °C

5: 92 percent / Et₃N / aq. ethanol / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; chloro-trimethyl-silane; ethanol; MeP(+)(OPh)3I(-); potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-12328

Reference yield:

1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine (146557-80-4) → [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid (179017-52-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / MeP(+)(OPh)3I(-); 2,6-lutidine / dimethylformamide / 20 °C

2: 94 percent / KHMDS / tetrahydrofuran / -78 - 20 °C

3: 87 percent / Me₃SiCl; EtOH / CHCl₃ / 20 °C

4: 92 percent / Et₃N / aq. ethanol / 20 °C

With 2,6-dimethylpyridine; chloro-trimethyl-silane; ethanol; MeP(+)(OPh)3I(-); potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-12328

upstream raw materials:

[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphinic acid ethyl ester

1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine

1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

5'-O-(tert-butydiphenylsilyl)-3'-deoxy-3'-C-(iodomethyl)thymidine

Downstream raw materials:

C₇₀H₈₄N₅O₁₂PSi₂

C₅₅H₇₀N₅O₁₀PSi₂

C₅₄H₆₈N₅O₁₀PSi₂

C₄₃H₅₀N₅O₁₂P