1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

Base Information

• Chemical Name: 1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil
• CAS No.: 847605-56-5
• Molecular Formula: C₂₇H₃₃N₃O₉Si
• Molecular Weight: 571.659
• Mol file: 847605-56-5.mol

Synonyms:1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

Chemical Property of 1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

There total 1 articles about 1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-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: 78.0%

2-nitrobenzyl chloride (610-14-0) + 1-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil (292636-95-4) → 1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil (847605-56-5)

Guidance literature:

With dmap; In pyridine; dichloromethane; for 24h; Heating;

DOI:10.1002/hlca.200490271

Reference yield: 100.0%

1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil (847605-56-5) → 1-[6,7-dideoxy-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil (847605-57-6)

Guidance literature:

With water; trifluoroacetic acid; at 80 ℃; for 1h;

DOI:10.1002/hlca.200490271

Reference yield:

1-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil (847605-56-5) → 1-[6,7-dideoxy-5-O-(4,4'-dimethoxytrityl)-7-C-(triethylsilyl)-3-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allo-hept-6-ynofuranosyl]uracil

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / CF₃COOH; H₂O / 1 h / 80 °C

2.1: 78 percent / 4-pyrrolidinopyridine / pyridine / 24 h / 23 °C

3.1: 62 percent / NH₄Cl; Zn powder / acetonitrile; H₂O / 7 h / 23 °C

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

4.2: 59 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

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

5.2: 16 percent / CH₂Cl₂; 1,2-dichloro-ethane / 1.17 h / 80 °C

With 2,4,6-trimethyl-pyridine; 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

upstream raw materials:

2-nitrobenzyl chloride

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

Downstream raw materials:

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

3-benzoyl-1-[2,3-di-O-benzoyl-6,7-dideoxy-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil

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

3-benzoyl-1-[2,3-di-O-benzoyl-6,7-dideoxy-5-O-(2-nitrobenzoyl)-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil