N₁-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide

Base Information

• Chemical Name: N₁-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide
• CAS No.: 596116-45-9
• Molecular Formula: C₂₃H₃₅N₃O₆SSi
• Molecular Weight: 509.699
• Mol file: 596116-45-9.mol

Synonyms:N₁-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide

Chemical Property of N₁-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N₁-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide

There total 2 articles about N₁-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide 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: 66.0%

5'-O-(t-butyldimethylsilyl)-2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine (117383-85-4) + toluene-4-sulfonamide (70-55-3) → N1-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide (596116-45-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 72h; Heating;

DOI:10.1016/S0040-4020(03)00589-1

Reference yield:

5'-O-t-butyl-dimethylsilyl-3'-O-methanesulfonyl-thymidine (117383-83-2) → N1-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide (596116-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / DBU / acetonitrile

2: 66 percent / DBU / acetonitrile / 72 h / Heating

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;

DOI:10.1016/S0040-4020(03)00589-1

Reference yield: 88.0%

N1-{1-[5-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-4-hydroxy-tetrahydro-2-furanyl]-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl}-4-methyl-1-benzenesulfonamide (596116-45-9) → 5-methyl-N2-tosyl-1-(2-deoxy-β-D-threopentofuranosyl)isocytosine

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4020(03)00589-1

upstream raw materials:

5'-O-(t-butyldimethylsilyl)-2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine

toluene-4-sulfonamide

5'-O-t-butyl-dimethylsilyl-3'-O-methanesulfonyl-thymidine