1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine

Base Information

• Chemical Name: 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine
• CAS No.: 183895-65-0
• Molecular Formula: C₃₀H₄₆N₂O₉Si₂
• Molecular Weight: 634.874
• Mol file: 183895-65-0.mol

Synonyms:1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine

Chemical Property of 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine

There total 5 articles about 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine 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: 95.0%

benzoyl cyanide (613-90-1) + 1-[4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]thymine (183436-73-9) → 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine (183895-65-0)

Guidance literature:

With triethylamine; In 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1080/07328319608002462

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine (183895-65-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) hexamethyldisilazane, 2.) SnCl₄ / 1.) pyridine, reflux, 6 h, 2.) 1,2-dichloroethane, 20 deg C, 16 h

2: 87 percent / NH₃ / methanol / 20 h / 20 °C

3: 91 percent / pyridine / 1.5 h / 20 °C

4: 95 percent / Et₃N / dioxane / 1 h / 20 °C

With ammonia; tin(IV) chloride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; pyridine; methanol;

DOI:10.1080/07328319608002462

Reference yield:

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3180-74-3) → 1-[2-O-benzoyl-4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]-thymine (183895-65-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / NH₃ / methanol / 20 h / 20 °C

2: 91 percent / pyridine / 1.5 h / 20 °C

3: 95 percent / Et₃N / dioxane / 1 h / 20 °C

With ammonia; triethylamine; In 1,4-dioxane; pyridine; methanol;

DOI:10.1080/07328319608002462

upstream raw materials:

benzoyl cyanide

1-[4,6-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranosyl]thymine

thymin

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate