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

Base Information

Chemical Name:3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose
CAS No.:79636-27-4
Molecular Formula:C₂₇H₃₃N₃O₁₃
Molecular Weight:607.571
Hs Code.:

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

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

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

There total 6 articles about 3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-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: 93.1%

: 108-24-7
acetic anhydride

: 79636-26-3
1,6-anhydro-2-azido-2-deoxy-4-O-(3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

: 79636-27-4
3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

Guidance literature:: With pyridine; at 0 ℃;
DOI:10.1248/cpb.29.1893

Reference yield:

: 100-39-0
benzyl bromide

: 79636-27-4
3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 85.1 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 0 deg C, 30 min, RT, 20 h

2: 85.1 percent / NaN₃, NH₄Cl / hexamethylphosphoric acid triamide; H₂O / 24 h / 110 °C

3: 63.2 percent / 8N KOH / dioxane; methanol / 3.5 h / Heating

4: 83.3 percent / H₂O / acetic acid / 2 h / 80 °C

5: 93.1 percent / pyridine / 0 °C

With pyridine; barium dihydroxide; potassium hydroxide; sodium azide; water; ammonium chloride; barium(II) oxide; In 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1248/cpb.29.1893

Reference yield:

: 78172-79-9
1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose

: 79636-27-4
3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 85.1 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 0 deg C, 30 min, RT, 20 h

2: 85.1 percent / NaN₃, NH₄Cl / hexamethylphosphoric acid triamide; H₂O / 24 h / 110 °C

3: 63.2 percent / 8N KOH / dioxane; methanol / 3.5 h / Heating

4: 83.3 percent / H₂O / acetic acid / 2 h / 80 °C

5: 93.1 percent / pyridine / 0 °C

With pyridine; barium dihydroxide; potassium hydroxide; sodium azide; water; ammonium chloride; barium(II) oxide; In 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1248/cpb.29.1893