ChemicalBook CAS DataBase List Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside

Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside synthesis

5synthesis methods

Product Name:Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside
CAS Number:53008-65-4
Molecular formula:C28H32O6
Molecular Weight:464.55

α-D-Glucopyranoside, methyl 2,3,4-tris-O-(phenylmethyl)-, 6-(2-nitrobenzeneacetate)

1223405-93-3
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Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside

53008-65-4
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$39.20/250MG

Yield:53008-65-4 84%

Reaction Conditions:

with ammonium chloride;zinc in tetrahydrofuran;methanol at 20; for 1 h;chemoselective reaction;Reagent/catalyst;Solvent;

Steps:

Deprotection of (2-nitrophenyl)acetate

Zn (26 mg, 0.398 mmol) and NH4Cl (12.8mg 0.24mmol) were added to the solution of methyl 2,3,4-tri-O-benzyl-6-O-(2-nitrophenyl)acetyl-α-D-glucopyranoside (50 mg, 0.079 mmol) in the mixture of THF (1.6 mL) and MeOH (0.4mL). The mixture was stirred for 1 h at rt. The mixture was diluted with CH2Cl2 (20 mL) and washed with 1 N aq. HCl, (10 mL) and with water (2 × 10 mL) the organic phase was dried(MgSO4), filtrated and concentrated. The product (A) was isolated after columnchromatography (hexane-EtOAc; 2:1) of the crude residue as a white solid (31 mg, 84 %)

References:

ágoston, Károly;ágoston, ágnes;Dorgan, Colin R.;Fügedi, Péter [Carbohydrate Research,2015,vol. 418,p. 98 - 103] Location in patent:supporting information