1,5-anhydro-4,6-O-benzylidene-2-(N⁴-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

Base Information

• Chemical Name: 1,5-anhydro-4,6-O-benzylidene-2-(N⁴-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol
• CAS No.: 705967-76-6
• Molecular Formula: C₃₁H₃₉N₃O₆Si
• Molecular Weight: 577.753

Synonyms:1,5-anhydro-4,6-O-benzylidene-2-(N⁴-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

Chemical Property of 1,5-anhydro-4,6-O-benzylidene-2-(N⁴-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

Chemical Property:

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Technology Process of 1,5-anhydro-4,6-O-benzylidene-2-(N⁴-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

There total 6 articles about 1,5-anhydro-4,6-O-benzylidene-2-(N⁴-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol 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: 92.0%

1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-(5-methylcytosin-1-yl)-D-altro-hexitol (705967-75-5) + benzoyl chloride (98-88-4) → 1,5-anhydro-4,6-O-benzylidene-2-(N4-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-76-6)

Guidance literature:

1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-(5-methylcytosin-1-yl)-D-altro-hexitol; benzoyl chloride; With pyridine; at 20 ℃;

With ammonium hydroxide; at 20 ℃; for 1h;

DOI:10.1081/NCN-120028338

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-(thymin-1-yl)-D-altro-hexitol (401906-49-8) → 1,5-anhydro-4,6-O-benzylidene-2-(N4-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / imidazole / dimethylformamide / 39 h / 70 °C

2.1: phosphorus oxychloride; 1,2,4-1H-triazole; pyridine / 3 h

2.2: 65 percent / aq. NH₃ / dioxane / 0.75 h

3.1: pyridine / 20 °C

3.2: 92 percent / aq. NH₃ / 1 h / 20 °C

With pyridine; 1H-imidazole; 1,2,4-Triazole; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120028338

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1,5-anhydro-4,6-O-benzylidene-2-(N4-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / imidazole / dimethylformamide / 39 h / 70 °C

2.1: phosphorus oxychloride; 1,2,4-1H-triazole; pyridine / 3 h

2.2: 65 percent / aq. NH₃ / dioxane / 0.75 h

3.1: pyridine / 20 °C

3.2: 92 percent / aq. NH₃ / 1 h / 20 °C

With pyridine; 1H-imidazole; 1,2,4-Triazole; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120028338

upstream raw materials:

1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-(5-methylcytosin-1-yl)-D-altro-hexitol

benzoyl chloride

1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-(thymin-1-yl)-D-altro-hexitol

1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-(thymin-1-yl)-D-altro-hexitol

Downstream raw materials:

1,5-anhydro-2-(N⁴-benzoyl-5-methylcytosin-1-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

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