allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

Base Information

• Chemical Name: allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate
• CAS No.: 245110-06-9
• Molecular Formula: C₃₉H₄₅N₃O₁₂
• Molecular Weight: 747.799

Synonyms:allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

Chemical Property of allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

There total 12 articles about allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate 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: 69.0%

acetic anhydride (108-24-7) + allyl O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate (245110-04-7) → allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate (245110-06-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at -40 ℃; for 6h;

DOI:10.1016/S0040-4020(99)00526-8

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose → allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate (245110-06-9)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 20 h

2: MeONa / methanol / 3 h

3: NaH / dimethylformamide

4: AcOH; ZnCl₂ / 4 h / 20 °C

5: Bu₄NF; AcOH / tetrahydrofuran / 25 h

6: 10 percent / K₂CO₃ / CH₂Cl₂ / 20 h

7: 83 percent / tert-butyldimethylsilyl triflate / toluene; CH₂Cl₂ / 0.5 h / -20 °C

8: CrO₃; aq. H₂SO₄ / acetone / 15 h / 0 °C

9: diethyl ether

10: MeONa / methanol / 5 h

11: 69 percent / pyridine; 4-(N,N'-dimethyl)aminopyridine / CH₂Cl₂ / 6 h / -40 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; dmap; sulfuric acid; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; potassium carbonate; acetic acid; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: silylation / 2: Deacetylation / 3: Alkylation / 4: debenzylation-acetylation / 5: desilylation / 6: Addition / 7: Condensation / 8: Oxidation / 9: Methylation / 10: Deacetylation / 11: Acetylation;

DOI:10.1016/S0040-4020(99)00526-8

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) → allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate (245110-06-9)

Guidance literature:

Multi-step reaction with 12 steps

1: NH₃ / tetrahydrofuran; methanol / 0 °C

2: imidazole / dimethylformamide / 20 h

3: MeONa / methanol / 3 h

4: NaH / dimethylformamide

5: AcOH; ZnCl₂ / 4 h / 20 °C

6: Bu₄NF; AcOH / tetrahydrofuran / 25 h

7: 10 percent / K₂CO₃ / CH₂Cl₂ / 20 h

8: 83 percent / tert-butyldimethylsilyl triflate / toluene; CH₂Cl₂ / 0.5 h / -20 °C

9: CrO₃; aq. H₂SO₄ / acetone / 15 h / 0 °C

10: diethyl ether

11: MeONa / methanol / 5 h

12: 69 percent / pyridine; 4-(N,N'-dimethyl)aminopyridine / CH₂Cl₂ / 6 h / -40 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; dmap; sulfuric acid; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; ammonia; sodium methylate; sodium hydride; potassium carbonate; acetic acid; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Deacetylation / 2: silylation / 3: Deacetylation / 4: Alkylation / 5: debenzylation-acetylation / 6: desilylation / 7: Addition / 8: Condensation / 9: Oxidation / 10: Methylation / 11: Deacetylation / 12: Acetylation;

DOI:10.1016/S0040-4020(99)00526-8

upstream raw materials:

acetic anhydride

allyl O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

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