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

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]-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester
• CAS No.: 195873-29-1
• Molecular Formula: C₃₅H₅₁N₂O₈PSi
• Molecular Weight: 686.858
• Mol file: 195873-29-1.mol

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

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]-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester

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]-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester

There total 3 articles about [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester 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: 94.0%

ethyl (1,1-diethoxyethyl)phosphinate (122085-76-1) + 5'-O-(tert-butydiphenylsilyl)-3'-deoxy-3'-C-(iodomethyl)thymidine (179015-84-0) → [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester (195873-29-1)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 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]-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester (195873-29-1)

Guidance literature:

Multi-step reaction with 3 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

With 2,6-dimethylpyridine; sodium tetrahydroborate; MeP(+)(OPh)3I(-); potassium hexamethylsilazane; In tetrahydrofuran; ethanol; 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]-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester (195873-29-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 2,6-dimethylpyridine; MeP(+)(OPh)3I(-); potassium hexamethylsilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-12328

upstream raw materials:

ethyl (1,1-diethoxyethyl)phosphinate

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

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

Downstream 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

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

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

C₄₄H₅₂N₅O₁₂P