1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

Base Information

Chemical Name:1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil
CAS No.:847605-63-4
Molecular Formula:C₄₈H₆₆N₂O₉Si₂
Molecular Weight:871.231
Hs Code.:

Synonyms:1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

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Chemical Property of 1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

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Technology Process of 1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

There total 7 articles about 1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil 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: 33.0%

: 217300-17-9
chloromethoxy-triisopropyl-silane

: 847605-62-3
1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

: 1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-3-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

: 847605-63-4
1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

Guidance literature:: 1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil; With dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 23 ℃; for 1.5h;

chloromethoxy-triisopropyl-silane; In dichloromethane; 1,2-dichloro-ethane; at 80 ℃; for 1.16667h;
DOI:10.1002/hlca.200490271

Reference yield:

: 292636-95-4
1-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

: 847605-63-4
1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

Guidance literature:: Multi-step reaction with 6 steps

1.1: 78 percent / 4-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 24 h / Heating

2.1: 100 percent / CF₃COOH; H₂O / 1 h / 80 °C

3.1: 78 percent / 4-pyrrolidinopyridine / pyridine / 24 h / 23 °C

4.1: 62 percent / NH₄Cl; Zn powder / acetonitrile; H₂O / 7 h / 23 °C

5.1: sym-collidine; AgNO₃ / CH₂Cl₂ / 23 °C

5.2: 59 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

6.1: (i-Pr)2NEt; Bu₂SnCl₂ / 1,2-dichloro-ethane / 1.5 h / 23 °C

6.2: 33 percent / CH₂Cl₂; 1,2-dichloro-ethane / 1.17 h / 80 °C

With 2,4,6-trimethyl-pyridine; dmap; dibutyltin chloride; water; ammonium chloride; 4-pyrrolidin-1-ylpyridine; silver nitrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; In pyridine; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1002/hlca.200490271

Reference yield:

: 847605-57-6
1-[6,7-dideoxy-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

: 847605-63-4
1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-2-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

Guidance literature:: Multi-step reaction with 4 steps

1.1: 78 percent / 4-pyrrolidinopyridine / pyridine / 24 h / 23 °C

2.1: 62 percent / NH₄Cl; Zn powder / acetonitrile; H₂O / 7 h / 23 °C

3.1: sym-collidine; AgNO₃ / CH₂Cl₂ / 23 °C

3.2: 59 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

4.1: (i-Pr)2NEt; Bu₂SnCl₂ / 1,2-dichloro-ethane / 1.5 h / 23 °C

4.2: 33 percent / CH₂Cl₂; 1,2-dichloro-ethane / 1.17 h / 80 °C

With 2,4,6-trimethyl-pyridine; dibutyltin chloride; ammonium chloride; 4-pyrrolidin-1-ylpyridine; silver nitrate; N-ethyl-N,N-diisopropylamine; zinc; In pyridine; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1002/hlca.200490271