3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol

Base Information

• Chemical Name: 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol
• CAS No.: 222723-63-9
• Molecular Formula: C₃₁H₄₀O₅Si
• Molecular Weight: 520.741
• Mol file: 222723-63-9.mol

Synonyms:3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol

Chemical Property of 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol

There total 1 articles about 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol 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: 76.0%

2,2-dimethoxy-propane (77-76-9) + 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-iditol (222408-79-9) → 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol (222723-63-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 1.5h;

DOI:10.1080/07328309908543990

Reference yield: 96.0%

acetic anhydride (108-24-7) + 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol (222723-63-9) → 2-O-acetyl-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol (222723-64-0)

Guidance literature:

With dmap; In pyridine; for 3h;

DOI:10.1080/07328309908543990

Reference yield:

3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol (222723-63-9) → 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-L-glucitol

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / DMAP / pyridine / 3 h

2: 92 percent / AcOH / H₂O / 16 h

3: 1.) SOCl₂, pyridine, 2.) RuCl₃, NaIO₄ / 1.) EtOAc, 0 deg C, 30 min, 2.) MeCN, CH₂Cl₂, H₂O, 15 min

4: 1.) LiOMe, 2.) H₂SO₄ / 1.) MeOH, 3 h, 2.) MeOH, H₂O, 50 deg C, 3 h

With pyridine; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; sulfuric acid; lithium methanolate; acetic acid; In pyridine; water;

DOI:10.1080/07328309908543990

upstream raw materials:

2,2-dimethoxy-propane

3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-iditol

Downstream raw materials:

2-O-acetyl-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-iditol

2,5-anhydro-3,4-di-O-benzyl-L-glucitol

2-O-acetyl-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-iditol

2-O-acetyl-3,4-di-O-benzyl-5,6-O-(cyclic sulfate)-1-deoxy-1-dimethylphenylsilyl-D-iditol