4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Base Information

• Chemical Name: 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• CAS No.: 131070-18-3
• Molecular Formula: C₃₂H₄₉NO₁₂
• Molecular Weight: 639.741
• Mol file: 131070-18-3.mol

Synonyms:4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Chemical Property of 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

There total 8 articles about 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 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:

2,3:5,6-Di-O-isopropylidene-4-O-(4',6'-O-isopropylidene-α-D-glucopyranosyl)-aldehydo-D-glucose dimethyl acetal (72200-55-6) → 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (131070-18-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / imidazole / dimethylformamide / 5 h / 0 deg C --> room temperature

2: 68 percent / pyridinium chlorochromate, potassium acetate / benzene / 2 h / Heating

3: 97 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O; acetic acid / 4 h

4: lithium aluminium hydride / tetrahydrofuran

5: 86 percent / methanol / 2 h

6: 1.) sodium hydride, 2.) tetrabutylammonium bromide / 1.) tetrahydrofuran, 0 deg C, 10 min, 2.) 12 h

With 1H-imidazole; lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetrabutylammomium bromide; potassium acetate; sodium acetate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; water; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0008-6215(90)80149-W

Reference yield:

4-O-(3-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (131070-11-6) → 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (131070-18-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / pyridinium chlorochromate, potassium acetate / benzene / 2 h / Heating

2: 97 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O; acetic acid / 4 h

3: lithium aluminium hydride / tetrahydrofuran

4: 86 percent / methanol / 2 h

5: 1.) sodium hydride, 2.) tetrabutylammonium bromide / 1.) tetrahydrofuran, 0 deg C, 10 min, 2.) 12 h

With lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetrabutylammomium bromide; potassium acetate; sodium acetate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; water; acetic acid; benzene;

DOI:10.1016/0008-6215(90)80149-W

Reference yield:

4-O-(3-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-α-D-arabino-hexopyranosyl-2-ulose)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (131070-13-8) → 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (131070-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O; acetic acid / 4 h

2: lithium aluminium hydride / tetrahydrofuran

3: 86 percent / methanol / 2 h

4: 1.) sodium hydride, 2.) tetrabutylammonium bromide / 1.) tetrahydrofuran, 0 deg C, 10 min, 2.) 12 h

With lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetrabutylammomium bromide; sodium acetate; sodium hydride; In tetrahydrofuran; methanol; water; acetic acid;

DOI:10.1016/0008-6215(90)80149-W

upstream raw materials:

benzyl bromide

4-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-gluco-pyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

2,3:5,6-Di-O-isopropylidene-4-O-(4',6'-O-isopropylidene-α-D-glucopyranosyl)-aldehydo-D-glucose dimethyl acetal

4-O-(3-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Downstream raw materials:

4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-L-idose dimethyl acetal

4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-5,6-di-O-acetyl-2,3-O-isopropylidene-aldehydo-L-idose dimethyl acetal

methyl uronate