allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside
• CAS No.: 753025-65-9
• Molecular Formula: C₅₁H₄₇N₃O₁₆
• Molecular Weight: 957.945
• Mol file: 753025-65-9.mol

Synonyms:allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside

Chemical Property of allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside

There total 5 articles about allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-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: 97.0%

allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-4,6-O-benzylidene-α-D-glucopyranoside (753025-63-7) → allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside (753025-65-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; for 5h; Heating;

DOI:10.1055/s-2004-829103

Reference yield:

2-(azidomethyl)benzoyl chloride (289712-58-9) → allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside (753025-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 52 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

3: 97 percent / p-TsOH / methanol; CH₂Cl₂ / 5 h / Heating

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1055/s-2004-829103

Reference yield:

allyl 4,6-O-benzylidene-α-D-glucopyranoside (93382-48-0) → allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside (753025-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 52 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

3: 97 percent / p-TsOH / methanol; CH₂Cl₂ / 5 h / Heating

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1055/s-2004-829103

upstream raw materials:

allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-4,6-O-benzylidene-α-D-glucopyranoside

allyl 4,6-O-benzylidene-α-D-glucopyranoside

2-(azidomethyl)benzoyl chloride

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

Downstream raw materials:

allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside