N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine
• CAS No.: 175915-89-6
• Molecular Formula: C₄₈H₄₇N₃O₈Si
• Molecular Weight: 822.002

Synonyms:N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine

Chemical Property of N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine

There total 5 articles about N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}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: 61.0%

4-N-benzoylcytosine (26661-13-2) + C38H42O7Si (175915-97-6) → N4-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine (175915-89-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 60 ℃; for 1h;

DOI:10.1021/ja952322m

Reference yield:

benzoyl chloride (98-88-4) → N4-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine (175915-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / pyridine, DMAP

2: 61 percent / trimethylsilyl triflate / acetonitrile / 1 h / 60 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1021/ja952322m

Reference yield:

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester (441044-21-9) → N4-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-6'-(tert-butyldiphenylsilyl)-3',5'-dideoxy-β-allofuranosyl}cytosine (175915-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / imidazole / tetrahydrofuran

2: 74 percent / pyridine, DMAP

3: 61 percent / trimethylsilyl triflate / acetonitrile / 1 h / 60 °C

With pyridine; 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja952322m

upstream raw materials:

4-N-benzoylcytosine

C₃₈H₄₂O₇Si

benzoyl chloride

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

Downstream raw materials:

C₃₂H₂₈BrN₃O₇

N⁴-benzoyl-1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-3',5'-dideoxy-β-allofuranosyl}cytosine

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