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

Base Information

• Chemical Name: 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-β-D-glucopyranose
• CAS No.: 929879-87-8
• Molecular Formula: C₂₈H₃₃N₃O₁₃
• Molecular Weight: 619.582
• Mol file: 929879-87-8.mol

Synonyms:1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-β-D-glucopyranose

Chemical Property of 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-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-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-β-D-glucopyranose

There total 3 articles about 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-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:

6-(4-azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid allyl ester + acetic anhydride (108-24-7) → 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-β-D-glucopyranose (929879-87-8)

Guidance literature:

With dmap; In sodium hydrogencarbonate; N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/chem.200601111

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose (796873-39-7) → 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-β-D-glucopyranose (929879-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaHCO₃; dimethylformamide / 12 h / 20 °C

2: 4-dimethylaminopyridine / aq. NaHCO₃; dimethylformamide / 12 h / 20 °C

With dmap; In sodium hydrogencarbonate; N,N-dimethyl-formamide;

DOI:10.1002/chem.200601111

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-(2,3,4-tri-O-acetyl-6-(2-propenyl)-β-D-glucopyranuronosyl)-β-D-glucopyranose (929879-87-8)

Guidance literature:

Multi-step reaction with 3 steps

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

2: aq. NaHCO₃; dimethylformamide / 12 h / 20 °C

3: 4-dimethylaminopyridine / aq. NaHCO₃; dimethylformamide / 12 h / 20 °C

With dmap; sodium hypochlorite; TEMPO; potassium bromide; In tetrahydrofuran; sodium hydrogencarbonate; N,N-dimethyl-formamide;

DOI:10.1002/chem.200601111

upstream raw materials:

acetic anhydride

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

Downstream raw materials:

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