5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

Base Information

Chemical Name:5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride
CAS No.:213480-41-2
Molecular Formula:C₁₈H₂₁NO₇
Molecular Weight:363.367
Hs Code.:

Synonyms:5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

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Chemical Property of 5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

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Technology Process of 5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

There total 5 articles about 5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride 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: 91.0%

: 213480-40-1
(2R,3R,4R,5R)-5-((3'S,4'R)-1-benzyl-3-hydroxyazetidin-2-one-4-yl)-3,4-dihydroxy-3,4-di-O-isopropylidene-2-methoxytetrahydrofuran

: 213480-41-2
5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In phosphate buffer; dichloromethane; at -5 - 0 ℃; pH=7;
DOI:10.1021/jo980354x

Reference yield:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 213480-41-2
5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

Guidance literature:: Multi-step reaction with 4 steps

1: 4A MS / CH₂Cl₂ / 1 h / 0 °C

2: 5.53 g / triethylamine / toluene; CH₂Cl₂ / 20 °C

3: 97 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

4: 91 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; hydrogen; triethylamine; potassium bromide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; toluene; 1: Condensation / 2: Cycloaddition / 3: Hydrogenolysis / 4: Oxidation;
DOI:10.1021/jo980354x

Reference yield:

: 100-46-9
benzylamine

: 213480-41-2
5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

Guidance literature:: Multi-step reaction with 4 steps

1: 4A MS / CH₂Cl₂ / 1 h / 0 °C

2: 5.53 g / triethylamine / toluene; CH₂Cl₂ / 20 °C

3: 97 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

4: 91 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; hydrogen; triethylamine; potassium bromide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; toluene; 1: Condensation / 2: Cycloaddition / 3: Hydrogenolysis / 4: Oxidation;
DOI:10.1021/jo980354x