4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile

Base Information

• Chemical Name: 4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile
• CAS No.: 213037-77-5
• Molecular Formula: C₂₉H₄₅N₃O₆Si₂
• Molecular Weight: 587.864
• Mol file: 213037-77-5.mol

Synonyms:4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile

Chemical Property of 4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile

There total 1 articles about 4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile 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: 38.0%

3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine (64911-18-8) + 4-cyanobenzaldehyde (105-07-7) → 4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile (213037-77-5)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01231-3

Reference yield: 90.0%

4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile (213037-77-5) → 4-{1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonyl}-benzonitrile (213037-78-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(98)01231-3

Reference yield:

4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile (213037-77-5) → 5-(p-cyanobenzoyl)-2'-deoxyuridine (213037-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2: 94 percent / TBAF / tetrahydrofuran

With tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(98)01231-3

upstream raw materials:

3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine

4-cyanobenzaldehyde

Downstream raw materials:

4-{1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonyl}-benzonitrile

5-(p-cyanobenzoyl)-2'-deoxyuridine