O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Base Information

• Chemical Name: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 543719-74-0
• Molecular Formula: C₄₄H₅₀N₄O₁₅Si
• Molecular Weight: 902.984
• Mol file: 543719-74-0.mol

Synonyms:O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property of O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 3 articles about O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 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: 84.0%

6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (543719-73-9) + 2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride (4163-45-5) → O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (543719-74-0)

Guidance literature:

With silver trifluoromethanesulfonate; tin(ll) chloride; In dichloromethane; toluene; at -10 - 20 ℃; for 16h;

DOI:10.1021/ja029346v

Reference yield:

2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (102816-23-9) → O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (543719-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 g / DIEA; DMAP / CH₂Cl₂ / 16 h

2: 84 percent / SnCl₂; AgOTf; 4A MS / CH₂Cl₂; toluene / 16 h / -10 - 20 °C

With dmap; silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; tin(ll) chloride; In dichloromethane; toluene;

DOI:10.1021/ja029346v

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide (102816-24-0) → O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (543719-74-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol / 16 h

2: 41 g / DIEA; DMAP / CH₂Cl₂ / 16 h

3: 84 percent / SnCl₂; AgOTf; 4A MS / CH₂Cl₂; toluene / 16 h / -10 - 20 °C

With dmap; sodium methylate; silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; tin(ll) chloride; In methanol; dichloromethane; toluene;

DOI:10.1021/ja029346v

upstream raw materials:

6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride

2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide