(2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine

Base Information

• Chemical Name: (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine
• CAS No.: 142235-94-7
• Molecular Formula: C₃₆H₄₄N₄O₆Si
• Molecular Weight: 656.854
• Mol file: 142235-94-7.mol

Synonyms:

Chemical Property of (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine

There total 2 articles about (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine 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:

3,4-dihydro-2H-pyran (110-87-2) + 3-iodo-1-<(1,1-dimethylethyl)diphenylsilyl>-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>pyrazolo<4,3-d>pyrimidine (142189-89-7) → 1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine (142189-92-2) + (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine (142189-91-1,142235-94-7,142235-95-8,142235-96-9) + 1,1'-bis(tetrahydropyran-2-yl)-7,7'-bis<(tetrahydropyran-2-yl)oxy>3,3'-bispyrimidine> (142189-93-3)

Guidance literature:

With tributyl-amine; triphenyl-arsane; 1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-erythro-pent-1-enitol; toluene-4-sulfonic acid; bis(dibenzylideneacetone)-palladium⁽⁰⁾; Yield given. Multistep reaction. Yields of byproduct given; 1) DMF, EtOAc, 50 deg C, 2 d, 2) DMF, 80 deg C, 72 h;

DOI:10.1021/jo00043a029

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + ((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2,3-dihydrofuran-2-yl)methanol (130277-32-6) + 3-iodo-1-<(1,1-dimethylethyl)diphenylsilyl>-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>pyrazolo<4,3-d>pyrimidine (142189-89-7) → 1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine (142189-92-2) + (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine (142189-91-1,142235-94-7,142235-95-8,142235-96-9) + 1,1'-bis(tetrahydropyran-2-yl)-7,7'-bis<(tetrahydropyran-2-yl)oxy>3,3'-bispyrimidine> (142189-93-3)

Guidance literature:

With tributyl-amine; triphenyl-arsane; toluene-4-sulfonic acid; Product distribution; 2) bis(dibenzylideneacetone)palladium⁽⁰⁾; multistep reaction; other conditions; other catalyst; effect of additives, regio- and stereospecifity;

DOI:10.1021/jo00043a029

Reference yield:

(2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine (142189-91-1,142235-94-7,142235-95-8,142235-96-9) → 3-<2'-deoxy-5'-O-<(1,1-dimethylethyl)dimethylsilyl>-3'-O--β-D-ribofuranosyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine (142190-00-9,142236-06-4,142236-07-5,142236-08-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 4N>F / tetrahydrofuran; acetic acid / 0.17 h / 0 °C

2: Na / acetonitrile; acetic acid / Ambient temperature

3: 79 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

4: 93 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00043a029

upstream raw materials:

3,4-dihydro-2H-pyran

((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2,3-dihydrofuran-2-yl)methanol

3-iodo-1-<(1,1-dimethylethyl)diphenylsilyl>-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>pyrazolo<4,3-d>pyrimidine

Downstream raw materials:

3-<2'-deoxy-5'-O-<(1,1-dimethylethyl)dimethylsilyl>-3'-O--β-D-ribofuranosyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine