methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

Base Information

Chemical Name:methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate
CAS No.:1447801-63-9
Molecular Formula:C₃₁H₃₆O₁₀
Molecular Weight:568.621
Hs Code.:

Synonyms:methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

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Chemical Property of methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

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Technology Process of methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

There total 5 articles about methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate 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%

: 1447801-87-7
methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

: 123-76-2
levulinic acid

: 1447801-63-9
methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1021/jo400467g

Reference yield:

: 98-88-4
benzoyl chloride

: 1447801-63-9
methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; pyridine / dichloromethane / -40 - 20 °C

2.1: hydrogen bromide / dichloromethane; acetic acid / 3 h / 0 °C

2.2: 20 h / 20 °C / Inert atmosphere

3.1: trimethyltin(IV) hydroxide / toluene / 1 h / 100 °C / Microwave irradiation

3.2: 60 °C / Microwave irradiation

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

With pyridine; dmap; hydrogen bromide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethyltin(IV) hydroxide; In dichloromethane; acetic acid; toluene;
DOI:10.1021/jo400467g

Reference yield:

: 87326-77-0,87326-78-1
methyl 3-O-benzyl-L-idopyranosyluronate

: 1447801-63-9
methyl 3-O-benzyl-4-O-levulinoyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-idopyranuronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; pyridine / dichloromethane / -40 - 20 °C

2.1: hydrogen bromide / dichloromethane; acetic acid / 3 h / 0 °C

2.2: 20 h / 20 °C / Inert atmosphere

3.1: trimethyltin(IV) hydroxide / toluene / 1 h / 100 °C / Microwave irradiation

3.2: 60 °C / Microwave irradiation

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

With pyridine; dmap; hydrogen bromide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethyltin(IV) hydroxide; In dichloromethane; acetic acid; toluene;
DOI:10.1021/jo400467g