ChemicalBook CAS DataBase List BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE synthesis

9synthesis methods

Product Name:BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
CAS Number:62867-63-4
Molecular formula:C29H33NO6
Molecular Weight:491.58

Benzyl 2-Deoxy-2-phthalimido-3,6-di-O-benzyl--D-glucopyranoside

80035-36-5
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$95.00/5mg

BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

62867-63-4
29 suppliers
$60.00/25mg

Yield:62867-63-4 740 mg

Reaction Conditions:

Stage #1: benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosidewith ethylenediamine in ethanol;Reflux;
Stage #2: with acetic anhydride in ethanol; for 3 h;

Steps:

Benzyl 2-Acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 4

A mixture of N-phthalimido compound 3 (1 g, 1.7 mmol) in EtOH (20 mL), containing1.2 mL of ethylenediamine, was refluxed overnight. After TLC (toluene -EtOAc4:1) showed the reaction was complete, the mixture was concentrated and re-dissolvedin 4:1 EtOH-Ac2O (25 mL). The mixture was stirred for 3 h and then concentrated.Chromatography of the residue (cyclohexane-EtOAc) gave 740 mg of monosaccharide4, whose NMR data were identical with those recently reported in literature.[19]

References:

Adamo, Roberto;Micoli, Francesca;Proietti, Daniela;Berti, Francesco [Synthetic Communications,2014,vol. 44,# 9,p. 1266 - 1273]