3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

Base Information

Chemical Name:3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine
CAS No.:174221-91-1
Molecular Formula:C₃₈H₄₅F₃N₄O₇Si
Molecular Weight:754.879
Hs Code.:

Synonyms:3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

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Chemical Property of 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

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Technology Process of 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

There total 9 articles about 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-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: 71.0%

: N-[(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-2,2,2-trifluoro-acetamide

: 174221-91-1
3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

Guidance literature:: With ammonium hydroxide; In tetrahydrofuran; for 6h; Ambient temperature;
DOI:10.1021/jo9510548

Reference yield:

: 3736-77-4
2,2'-Anhydrouridine

: 174221-91-1
3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

Guidance literature:: Multi-step reaction with 7 steps

1: 56 percent / DMAP / pyridine / 16 h / Ambient temperature

2: 43 percent / NaH / 16 h / 90 °C

3: 79 percent / aq. NaOH / ethanol / 16 h / Heating

4: 55 percent / Et₃N / acetonitrile / 16 h / Ambient temperature

5: Et₃N / acetonitrile / 3 h / Ambient temperature

6: phosphorus oxychloride, Et₃N / acetonitrile / 3 h / Ambient temperature

7: 71 percent / NH₄OH / tetrahydrofuran / 6 h / Ambient temperature

With dmap; ammonium hydroxide; sodium hydroxide; sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; ethanol; acetonitrile;
DOI:10.1021/jo9510548

Reference yield:

: 174221-82-0
5'-O-(4,4'-dimethoxytrityl)-2'-N,3'-O-(2-(trichloromethyl)oxazolino)-2'-deoxy-1-(β-D-ribofuranosyl)uracil

: 174221-91-1
3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / aq. NaOH / ethanol / 16 h / Heating

2: 55 percent / Et₃N / acetonitrile / 16 h / Ambient temperature

3: Et₃N / acetonitrile / 3 h / Ambient temperature

4: phosphorus oxychloride, Et₃N / acetonitrile / 3 h / Ambient temperature

5: 71 percent / NH₄OH / tetrahydrofuran / 6 h / Ambient temperature

With ammonium hydroxide; sodium hydroxide; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; acetonitrile;
DOI:10.1021/jo9510548