1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine

Base Information

Chemical Name:1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine
CAS No.:321155-88-8
Molecular Formula:C₃₇H₄₅N₃O₅Si
Molecular Weight:639.867
Hs Code.:

Synonyms:1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine

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Chemical Property of 1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine

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Technology Process of 1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine

There total 7 articles about 1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-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: 93.0%

: 321155-87-7
1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

: 321155-88-8
1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine

Guidance literature:: 1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil; With dmap; 2,4,6-triisopropylphenylsulfonyl chloride; triethylamine; In acetonitrile; at 20 ℃; for 4h;

With ammonium hydroxide; In acetonitrile; at 20 ℃; for 2h; Further stages.;
DOI:10.1021/jo000967l

Reference yield:

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

: 321155-88-8
1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / TsOH*H₂O; NaI / acetone / 2.5 h / 50 °C

2.1: 65 percent / pyridine / 94 h / 20 °C

3.1: 84 percent / Et₃N; DMAP / toluene / 1 h / 20 °C

4.1: (Me₃Sn)2; AIBN / benzene / 5 h / 80 °C

4.2: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: Et₃N; DMAP / toluene / 20 h / 20 °C

6.1: 2,4,6-triisopropylbenzenesulfonyl chloride; DMAP; Et₃N / acetonitrile / 4 h / 20 °C

6.2: 93 percent / aq. NH₃ / acetonitrile / 2 h / 20 °C

With pyridine; dmap; 2,4,6-triisopropylphenylsulfonyl chloride; 2,2'-azobis(isobutyronitrile); hexamethyldistannane; toluene-4-sulfonic acid; triethylamine; sodium iodide; In acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo000967l

Reference yield:

: 4753-03-1
1-(2-deoxy-2-iodo-β-D-ribofuranosyl)uracil

: 321155-88-8
1-[5-O-(4-methoxytrityl)-2-deoxy-2-vinyl-3-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]cytosine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 65 percent / pyridine / 94 h / 20 °C

2.1: 84 percent / Et₃N; DMAP / toluene / 1 h / 20 °C

3.1: (Me₃Sn)2; AIBN / benzene / 5 h / 80 °C

3.2: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

4.1: Et₃N; DMAP / toluene / 20 h / 20 °C

5.1: 2,4,6-triisopropylbenzenesulfonyl chloride; DMAP; Et₃N / acetonitrile / 4 h / 20 °C

5.2: 93 percent / aq. NH₃ / acetonitrile / 2 h / 20 °C

With pyridine; dmap; 2,4,6-triisopropylphenylsulfonyl chloride; 2,2'-azobis(isobutyronitrile); hexamethyldistannane; triethylamine; In toluene; acetonitrile; benzene;
DOI:10.1021/jo000967l