tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 444119-00-0
• Molecular Formula: C₂₇H₄₇N₃O₆Si₂
• Molecular Weight: 565.858
• Mol file: 444119-00-0.mol

Synonyms:tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside

Chemical Property of tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside

There total 9 articles about tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside 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: 98.0%

t-butyldimethylsiyl triflate (69739-34-0) + 6-O-acetyl-2-azido-3-O-benzyl-4-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside (444118-29-0) → tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside (444119-00-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; Inert atmosphere;

DOI:10.1002/anie.201306968

Reference yield:

2,6-dimethylpyridine (108-48-5) + t-butyldimethylsiyl triflate (69739-34-0) + 6-O-acetyl-2-azido-3-O-benzyl-4-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside (444118-29-0) → tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside (444119-00-0)

Guidance literature:

In dichloromethane;

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose → tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside (444119-00-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 29.8 g / imidazole / CH₂Cl₂ / 2 h

2: NaOMe; MeOH / 0.25 h

3: 29.0 g / p-TsOH*H₂O / acetonitrile / 20 °C

4: 95 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 8 h

5: 92 percent / aq. TFA / CH₂Cl₂ / 8.5 h / 20 °C

6: 96 percent / 2,4,6-collidine / -40 °C

7: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; methanol; 4 A molecular sieve; sodium methylate; toluene-4-sulfonic acid; trifluoroacetic acid; silver(l) oxide; In dichloromethane; acetonitrile;

DOI:10.1002/chem.200390009

upstream raw materials:

t-butyldimethylsiyl triflate

6-O-acetyl-2-azido-3-O-benzyl-4-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose