N⁴-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine
• CAS No.: 82845-97-4
• Molecular Formula: C₂₈H₄₅N₃O₆Si₂
• Molecular Weight: 575.853

Synonyms:N⁴-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

Chemical Property of N⁴-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

There total 4 articles about N⁴-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine 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: 91.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1-(β-D-arabinofuranosyl)-N4-benzoylcytosine (16640-05-4) → N4-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine (82845-97-4)

Guidance literature:

With 3-picoline-N-oxide; silver nitrate; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)87243-3

Reference yield: 83.0%

N4-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-2'-ulosyl]cytosine → N4-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine (82845-97-4)

Guidance literature:

With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 20 ℃; for 3.5h; stereoselective reaction;

DOI:10.1080/15257770.2017.1414240

Reference yield: 70.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1-(β-D-arabinofuranosyl)-N4-benzoylcytosine (16640-05-4) → N4-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine (82845-97-4) + N-{1-[(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide (82845-93-0)

Guidance literature:

With pyridine; silver nitrate; In tetrahydrofuran; for 3h; Product distribution; further solvents, reaction times, reagents;

upstream raw materials:

tert-butyldimethylsilyl chloride

1-(β-D-arabinofuranosyl)-N⁴-benzoylcytosine

N⁴-benzoyl-3',5'-di-O-tert-butyldimethylsilylcytidine

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