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

Base Information

• Chemical Name: 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose
• CAS No.: 796873-39-7
• Molecular Formula: C₁₉H₂₃N₃O₁₀
• Molecular Weight: 453.406
• Mol file: 796873-39-7.mol

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

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

There total 4 articles about 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-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:

β-D-glucopyranosyl-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (796873-51-3) → 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose (796873-39-7)

Guidance literature:

With sodium hypochlorite; 1,2,6,6-tetramethylpiperidine-1-oxide; potassium bromide; In tetrahydrofuran; sodium hydrogencarbonate; at 20 ℃; for 0.5h;

DOI:10.1016/j.carres.2004.07.018

Reference yield:

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-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose (796873-39-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

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

With sodium hypochlorite; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; sodium methylate; silver trifluoromethanesulfonate; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; sodium hydrogencarbonate;

DOI:10.1016/j.carres.2004.07.018

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (55682-57-0) → 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose (796873-39-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

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

With sodium hypochlorite; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; sodium methylate; silver trifluoromethanesulfonate; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; sodium hydrogencarbonate;

DOI:10.1016/j.carres.2004.07.018

upstream 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-β-D-glucopyranose

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

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

Downstream raw materials:

[6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate

methyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

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

methyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside