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

Base Information

• Chemical Name: 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
• CAS No.: 131070-30-9
• Molecular Formula: C₃₈H₅₅NO₁₅
• Molecular Weight: 765.852
• Mol file: 131070-30-9.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 19 articles about 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 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:

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) → 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 (131070-30-9)

Guidance literature:

Multi-step reaction with 17 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

15: methyl sulfoxide, dicyclohexylcarbodi-imide, pyridinium trifluoroacetate / 6 h

16: sodium chlorite, 2 M sulfamic acid, potassium acetate / dioxane / 2 h

17: CH₂Cl₂; diethyl ether / 2 h

With pyridine; sodium chlorite; lithium aluminium tetrahydride; 2,2'-dimethylaminopyridine; aminosulfonic acid; hydroxylamine hydrochloride; tetrabutylammomium bromide; sodium methylate; potassium acetate; sodium acetate; pyridinium trifluroacetate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetic acid; benzene;

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) → 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 (131070-30-9)

Guidance literature:

Multi-step reaction with 18 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

16: methyl sulfoxide, dicyclohexylcarbodi-imide, pyridinium trifluoroacetate / 6 h

17: sodium chlorite, 2 M sulfamic acid, potassium acetate / dioxane / 2 h

18: CH₂Cl₂; diethyl ether / 2 h

With pyridine; 1H-imidazole; sodium chlorite; lithium aluminium tetrahydride; 2,2'-dimethylaminopyridine; aminosulfonic acid; hydroxylamine hydrochloride; tetrabutylammomium bromide; sodium methylate; potassium acetate; sodium acetate; pyridinium trifluroacetate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; 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-arabino-hexopyranosyl-2-ulose)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (131070-13-8) → 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 (131070-30-9)

Guidance literature:

Multi-step reaction with 16 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

5: 73 percent / pyridinium p-toluenesulfonate / methanol / 8 h

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

7: 68 percent / aq. 80 percent acetic acid / 5 h / 40 °C

8: 74 percent / pyridine / CH₂Cl₂ / 3 h

9: potassium acetate / 20 h / 120 °C

10: sodium methoxide / methanol

11: 95 percent / 2,2'-dimethylaminopyridine, pyridine / CH₂Cl₂ / 8 h

12: 92 percent / 2,2'-dimethylaminopyridine, dicyclohexylcarbodi-imide / tetrahydrofuran / 4 h

13: 96 percent / aq. 80 percent acetic acid / 10 h / Ambient temperature

14: methyl sulfoxide, dicyclohexylcarbodi-imide, pyridinium trifluoroacetate / 6 h

15: sodium chlorite, 2 M sulfamic acid, potassium acetate / dioxane / 2 h

16: CH₂Cl₂; diethyl ether / 2 h

With pyridine; sodium chlorite; lithium aluminium tetrahydride; 2,2'-dimethylaminopyridine; aminosulfonic acid; hydroxylamine hydrochloride; tetrabutylammomium bromide; sodium methylate; potassium acetate; sodium acetate; pyridinium trifluroacetate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetic acid;

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

upstream raw materials:

diazomethane

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 uronate

methyl uronate

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