N⁴-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine

Base Information

• Chemical Name: N⁴-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine
• CAS No.: 219618-99-2
• Molecular Formula: C₆₈H₈₂N₄O₇Si₃
• Molecular Weight: 1151.68

Synonyms:N⁴-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine

Chemical Property of N⁴-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine

Chemical Property:

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Technology Process of N⁴-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine

There total 6 articles about N⁴-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine 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: 97.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'--3'-deoxycytidine (219618-97-0) → N4-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine (219618-99-2)

Guidance literature:

With triethylamine; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1021/jm980466g

Reference yield:

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine (90813-54-0) → N4-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine (219618-99-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / NH₂OH*HCl, pyridine / 0.33 h / Ambient temperature

2: 99 percent / 80 percent aq. TFA / 0.5 h / 0 °C

3: 92 percent / NaBH₄, AcOH / 2 h / 0 °C

4: 90 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

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

6: 97 percent / Et₃N / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; ammonium hydroxide; sodium tetrahydroborate; Triphenylsilyl chloride; hydroxylamine hydrochloride; acetic acid; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980466g

Reference yield:

1-<2-O-(tert-butyldimethylsilyl)-3-deoxy-3-(hydroxyimino)-β-D-erythro-pentofuranosyl>uracil (218967-30-7) → N4-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'-<(tert-butyldiphenylsilyl)oxyamino>-3'-deoxycytidine (219618-99-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / NaBH₄, AcOH / 2 h / 0 °C

2: 90 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

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

4: 97 percent / Et₃N / CH₂Cl₂ / 6 h / Ambient temperature

With 1H-imidazole; dmap; ammonium hydroxide; sodium tetrahydroborate; Triphenylsilyl chloride; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980466g

upstream raw materials:

4,4'-dimethoxytrityl chloride

2'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-3'--3'-deoxycytidine

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine

1-<2-O-(tert-butyldimethylsilyl)-3-deoxy-3-(hydroxyimino)-β-D-erythro-pentofuranosyl>uracil

Downstream raw materials:

N⁴-(4,4'-dimethoxytrityl)-3'-deoxy-3'-(hydroxylamino)cytidine

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