1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose
• CAS No.: 796873-38-6
• Molecular Formula: C₄₇H₄₁N₃O₁₃
• Molecular Weight: 855.855
• Mol file: 796873-38-6.mol

Synonyms:1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose

Chemical Property of 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose

There total 1 articles about 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose 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: 74.0%

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (55682-57-0) + methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (104707-00-8) → 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose (796873-38-6)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/j.carres.2004.07.018

Reference yield: 100.0%

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose (796873-38-6) → β-D-glucopyranosyl-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (796873-51-3)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 48h;

DOI:10.1016/j.carres.2004.07.018

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose (796873-38-6) → 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-D-glucopyranose

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

2: KBr; 1,2,6,6-tetramethylpiperidine-1-oxide; NaOCl / aq. NaHCO₃; tetrahydrofuran / 0.5 h / 20 °C

3: dimethylformamide / 12 h

4: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

5: 100 percent / TFA / 12 h / 20 °C

6: 65 percent / benzylamine / diethyl ether / 1 h / 0 °C

With dmap; sodium hypochlorite; 1,2,6,6-tetramethylpiperidine-1-oxide; sodium methylate; benzylamine; trifluoroacetic acid; potassium bromide; In tetrahydrofuran; methanol; diethyl ether; sodium hydrogencarbonate; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2004.07.018

upstream raw materials:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

β-D-glucopyranosyl-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose

methyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose