allyl O-(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 O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate
CAS No.:245110-04-7
Molecular Formula:C₃₇H₄₃N₃O₁₁
Molecular Weight:705.762
Hs Code.:

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

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

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

There total 11 articles about allyl O-(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:

: 245109-89-1
allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronate

: 245110-04-7
allyl O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

Guidance literature:: With sodium methylate; In methanol; for 5h;
DOI:10.1016/S0040-4020(99)00526-8

Reference yield:

: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 245110-04-7
allyl O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

Guidance literature:: Multi-step reaction with 10 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

With 1H-imidazole; chromium(VI) oxide; 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;
DOI:10.1016/S0040-4020(99)00526-8

Reference yield:

: 171032-74-9
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 245110-04-7
allyl O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-3-O-benzyl-α-L-idopyranosiduronate

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; chromium(VI) oxide; 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;
DOI:10.1016/S0040-4020(99)00526-8