4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside
CAS No.:1352561-57-9
Molecular Formula:C₃₉H₄₀O₈S
Molecular Weight:668.808
Hs Code.:

Synonyms:4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

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Chemical Property of 4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

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Technology Process of 4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

There total 9 articles about 4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-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: 90.0%

: 942044-42-0
(4-methylphenyl) 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

: 123-76-2
levulinic acid

: 1352561-57-9
4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

Guidance literature:: With dmap; diisopropyl-carbodiimide; In dichloromethane; for 48h; Inert atmosphere;
DOI:10.3762/bjoc.12.139

Reference yield:

: 582-52-5
1,2:5,6-diacetone-D-glucose

: 1352561-57-9
4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 18 h / 0 - 20 °C / Inert atmosphere

2.1: Amberlite IR-120 (H+ form) / water / 15 h / 70 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / 20 h / 0 °C / Inert atmosphere

4.1: sodium methylate / methanol / 120 h / Inert atmosphere

5.1: toluene-4-sulfonic acid / acetonitrile / 2 h / Inert atmosphere

6.1: diisopropyl-carbodiimide; dmap / dichloromethane / 96 h / Inert atmosphere

7.1: triethylsilane; trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C / Inert atmosphere

8.1: diisopropyl-carbodiimide; dmap / dichloromethane / 48 h / Inert atmosphere

With triethylsilane; dmap; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; trifluoroacetic anhydride; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.3762/bjoc.12.139

Reference yield:

: 101475-83-6
3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

: 1352561-57-9
4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: Amberlite IR-120 (H+ form) / water / 15 h / 70 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 20 h / 0 °C / Inert atmosphere

3.1: sodium methylate / methanol / 120 h / Inert atmosphere

4.1: toluene-4-sulfonic acid / acetonitrile / 2 h / Inert atmosphere

5.1: diisopropyl-carbodiimide; dmap / dichloromethane / 96 h / Inert atmosphere

6.1: triethylsilane; trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: diisopropyl-carbodiimide; dmap / dichloromethane / 48 h / Inert atmosphere

With triethylsilane; dmap; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; trifluoroacetic acid; trifluoroacetic anhydride; diisopropyl-carbodiimide; In methanol; dichloromethane; water; acetonitrile;
DOI:10.3762/bjoc.12.139