4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine

Base Information

• Chemical Name: 4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine
• CAS No.: 305819-96-9
• Molecular Formula: C₃₂H₃₆N₃O₈PSi
• Molecular Weight: 649.712

Synonyms:4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine

Chemical Property of 4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine

Chemical Property:

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Technology Process of 4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine

There total 2 articles about 4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)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: 78.0%

N-{1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-oxo-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide (139244-41-0) → 4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine (305819-96-9)

Guidance literature:

With tris(trimethylsilyl) phosphite; In dichloromethane; at 20 ℃;

DOI:10.1080/15257770008035038

Reference yield:

N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (139244-40-9) → 4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine (305819-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin reagent / CH₂Cl₂ / 0 - 20 °C

2: 78 percent / P(OSiMe₃)3 / CH₂Cl₂ / 20 °C

With tris(trimethylsilyl) phosphite; Dess-Martin periodane; In dichloromethane; 1: Oxidation / 2: Addition;

DOI:10.1080/15257770008035038

Reference yield:

4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)cytosine (305819-96-9) → [(2R,3S,5R)-5-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-yl]-phosphonic acid

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 24h;

DOI:10.1080/15257770008035038

upstream raw materials:

N-{1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-oxo-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

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