5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine

Base Information

• Chemical Name: 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine
• CAS No.: 219618-65-2
• Molecular Formula: C₃₂H₅₀N₄O₅Si₃
• Molecular Weight: 655.029
• Mol file: 219618-65-2.mol

Synonyms:5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine

Chemical Property of 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine

There total 7 articles about 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine 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:

2'-(benzyloxyamino)-5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxyuridine (175013-53-3) → 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine (219618-65-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 79 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / Ambient temperature

2: 100 percent / PPTS / tetrahydrofuran / 11 h / Ambient temperature

3: 81 percent / Cs₂CO₃ / methanol / 24 h / Ambient temperature

4: 83 percent / TsOH*H₂O / methanol / 72 h / Ambient temperature

5: 2.) NaBH₃CN / 1.) H₂O, MeOH, RT, 3 h, 2.) H₂O, MeOH, 15 h

6: Et₃N, DMAP / acetonitrile / 2 h / Ambient temperature

7: 1.) Et₃N, TPSCl, DMAP, 2.) NH₄OH / 1.) MeCN, RT, 3 h, 2.) MeCN, 2 h

With dmap; ammonium hydroxide; Triphenylsilyl chloride; hydrogen; pyridinium p-toluenesulfonate; sodium cyanoborohydride; caesium carbonate; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetonitrile;

DOI:10.1021/jm980466g

Reference yield:

5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine (175013-49-7) → 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine (219618-65-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / PPTS / tetrahydrofuran / 11 h / Ambient temperature

2: 81 percent / Cs₂CO₃ / methanol / 24 h / Ambient temperature

3: 83 percent / TsOH*H₂O / methanol / 72 h / Ambient temperature

4: 2.) NaBH₃CN / 1.) H₂O, MeOH, RT, 3 h, 2.) H₂O, MeOH, 15 h

5: Et₃N, DMAP / acetonitrile / 2 h / Ambient temperature

6: 1.) Et₃N, TPSCl, DMAP, 2.) NH₄OH / 1.) MeCN, RT, 3 h, 2.) MeCN, 2 h

With dmap; ammonium hydroxide; Triphenylsilyl chloride; pyridinium p-toluenesulfonate; sodium cyanoborohydride; caesium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jm980466g

Reference yield:

5'-O-(tert-butyldiphenylsilyl)-2'-deoxy-2'-<(2-tetrahydrofuranyl)oxyamino>uridine (214055-28-4) → 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine (219618-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / TsOH*H₂O / methanol / 72 h / Ambient temperature

2: 2.) NaBH₃CN / 1.) H₂O, MeOH, RT, 3 h, 2.) H₂O, MeOH, 15 h

3: Et₃N, DMAP / acetonitrile / 2 h / Ambient temperature

4: 1.) Et₃N, TPSCl, DMAP, 2.) NH₄OH / 1.) MeCN, RT, 3 h, 2.) MeCN, 2 h

With dmap; ammonium hydroxide; Triphenylsilyl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; In methanol; acetonitrile;

DOI:10.1021/jm980466g

upstream raw materials:

2'-(benzyloxyamino)-5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxyuridine

5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine

5'-O-(tert-butyldiphenylsilyl)-2'-deoxy-2'-(N-hydroxylamino)uridine

5'-O-(tert-butyldiphenylsilyl)-2'-deoxy-2'-<(2-tetrahydrofuranyl)oxyamino>uridine