5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside

Base Information

• Chemical Name: 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside
• CAS No.: 1388151-16-3
• Molecular Formula: C₄₂H₅₈O₁₅
• Molecular Weight: 802.914

Synonyms:5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside

Chemical Property of 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside

There total 11 articles about 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside 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:

1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose (67313-50-2) → 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside (1388151-16-3) + 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-α-D-glucopyranoside (1388150-92-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydride / 1,2-dimethoxyethane / 5.25 h / 0 - 85 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 - 20 °C

2.2: 1 h / 0 - 20 °C

3.1: hydrogenchloride; water / methanol / 1.5 h / 0 - 20 °C

4.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 0.25 h / -20 °C

5.1: water; acetic acid / 1,2-dichloro-ethane / 2 h / 60 °C

6.1: sodium hydrogencarbonate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / tetrahydrofuran / 3.25 h / 0 - 20 °C

6.2: 16 h / 0 - 20 °C

7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

8.1: trifluoroacetic acid / 16 h / 0 - 20 °C

9.1: morpholine; acetic acid / toluene / 6.25 h / 0 - 20 °C

10.1: caesium carbonate / dichloromethane / 1.5 h / 0 - 20 °C

11.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

11.2: 0.75 h / -20 °C

12.1: dichlorotetrakis(1,1- dimethylethyl)di-μ-hydroxyditin / tetrahydrofuran; methanol / 40 h / 20 °C / Inert atmosphere

With morpholine; hydrogenchloride; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; sodium hydride; sodium hydrogencarbonate; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; dichlorotetrakis(1,1- dimethylethyl)di-μ-hydroxyditin; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

Reference yield:

1,6-anhydro-2-O-butyl-4-O-(2-tetrahydropyranyl)-β-D-glucopyranose (1388150-81-9) → 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside (1388151-16-3) + 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-α-D-glucopyranoside (1388150-92-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 - 20 °C

1.2: 1 h / 0 - 20 °C

2.1: hydrogenchloride; water / methanol / 1.5 h / 0 - 20 °C

3.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 0.25 h / -20 °C

4.1: water; acetic acid / 1,2-dichloro-ethane / 2 h / 60 °C

5.1: sodium hydrogencarbonate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / tetrahydrofuran / 3.25 h / 0 - 20 °C

5.2: 16 h / 0 - 20 °C

6.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

7.1: trifluoroacetic acid / 16 h / 0 - 20 °C

8.1: morpholine; acetic acid / toluene / 6.25 h / 0 - 20 °C

9.1: caesium carbonate / dichloromethane / 1.5 h / 0 - 20 °C

10.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

10.2: 0.75 h / -20 °C

11.1: dichlorotetrakis(1,1- dimethylethyl)di-μ-hydroxyditin / tetrahydrofuran; methanol / 40 h / 20 °C / Inert atmosphere

With morpholine; hydrogenchloride; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; sodium hydride; sodium hydrogencarbonate; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; dichlorotetrakis(1,1- dimethylethyl)di-μ-hydroxyditin; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

Reference yield:

(methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-O-butyl-3-O-methyl-α/β-D-glucopyranose → 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-β-D-glucopyranoside (1388151-16-3) + 5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-α-D-glucopyranoside (1388150-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: caesium carbonate / dichloromethane / 1.5 h / 0 - 20 °C

2.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 0.75 h / -20 °C

3.1: dichlorotetrakis(1,1- dimethylethyl)di-μ-hydroxyditin / tetrahydrofuran; methanol / 40 h / 20 °C / Inert atmosphere

With caesium carbonate; dichlorotetrakis(1,1- dimethylethyl)di-μ-hydroxyditin; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose

1,6-anhydro-2-O-butyl-4-O-(2-tetrahydropyranyl)-β-D-glucopyranose

1,6-anhydro-2-O-butyl-3-O-methyl-4-O-(2-tetrahydropyranyl)-β-D-glucopyranose

1,6-anhydro-2-O-butyl-3-O-methyl-β-D-glucopyranose

Downstream raw materials:

5-phenylpentyl (methyl 2-O-benzoyl-4-O-levulinoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside

5-phenylpentyl (methyl 2-O-benzoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2-O-butyl-3-O-methyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside

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