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

Base Information

• Chemical Name: 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose dimethyl acetal
• CAS No.: 131070-29-6
• Molecular Formula: C₃₇H₅₅NO₁₄
• Molecular Weight: 737.842
• Mol file: 131070-29-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose 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: 96.0%

4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-6-O-p-anisyldiphenylmethyl-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose dimethyl acetal (131070-28-5) → 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose dimethyl acetal (131070-29-6)

Guidance literature:

With acetic acid; for 10h; Ambient temperature;

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

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-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose dimethyl acetal (131070-29-6)

Guidance literature:

Multi-step reaction with 15 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

7: 73 percent / pyridinium p-toluenesulfonate / methanol / 8 h

8: 1.) sodium hydride / 1.) tetrahydrofuran, 10 min, 2.) 18 h, 60 deg C

9: 68 percent / aq. 80 percent acetic acid / 5 h / 40 °C

10: 74 percent / pyridine / CH₂Cl₂ / 3 h

11: potassium acetate / 20 h / 120 °C

12: sodium methoxide / methanol

13: 95 percent / 2,2'-dimethylaminopyridine, pyridine / CH₂Cl₂ / 8 h

14: 92 percent / 2,2'-dimethylaminopyridine, dicyclohexylcarbodi-imide / tetrahydrofuran / 4 h

15: 96 percent / aq. 80 percent acetic acid / 10 h / Ambient temperature

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; 2,2'-dimethylaminopyridine; hydroxylamine hydrochloride; tetrabutylammomium bromide; sodium methylate; potassium acetate; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; 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-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose dimethyl acetal (131070-29-6)

Guidance literature:

Multi-step reaction with 14 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

6: 73 percent / pyridinium p-toluenesulfonate / methanol / 8 h

7: 1.) sodium hydride / 1.) tetrahydrofuran, 10 min, 2.) 18 h, 60 deg C

8: 68 percent / aq. 80 percent acetic acid / 5 h / 40 °C

9: 74 percent / pyridine / CH₂Cl₂ / 3 h

10: potassium acetate / 20 h / 120 °C

11: sodium methoxide / methanol

12: 95 percent / 2,2'-dimethylaminopyridine, pyridine / CH₂Cl₂ / 8 h

13: 92 percent / 2,2'-dimethylaminopyridine, dicyclohexylcarbodi-imide / tetrahydrofuran / 4 h

14: 96 percent / aq. 80 percent acetic acid / 10 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; 2,2'-dimethylaminopyridine; hydroxylamine hydrochloride; tetrabutylammomium bromide; sodium methylate; potassium acetate; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; benzene;

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

upstream raw materials:

4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-6-O-p-anisyldiphenylmethyl-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose 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

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

Downstream raw materials:

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

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

methyl uronate

methyl uronate