Reacción #217188

Ecuación de reacción

Compound [ 13 ]

1-Thiophenyl-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1-4)-2-deoxy-2-acetamido-β-D-glucopyranose

compound [ 17 ]

1-Thiophenyl-2,3,4-tri-O-benzyl-β-L-fucose

tin(II) chloride

→

compound [ 18 ]

1-Thiophenyl-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1-4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)]-2-deoxy-2-acetamido-β-D-glucopyranose

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture is subsequently filtered

Procedimiento

Compound [13] (0.2-4.81 g, 0.234-5.78 mmol) is dissolved with compound [17] (0.17-4.15 g, 0.37-9.25 mmol) in dry diethyl ether (5-100 ml) and stirred with 4 Å molecular sieves (0.1-6.8 g), silver perchlorate (0.15-3.59 g 0.702-17.34 mmol) and tin(II) chloride (0.13-3.29 g, 0.702-17.34 mmol) until the reaction is complete. The mixture is subsequently filtered, and the crude product compound [18] obtained after concentration is purified by chromatography on silica gel with an ethyl acetate/isohexane gradient (0.25-6.2 g, 0.2-4.91 mmol, about 85% yield). FAB-MS: M+H+ =1262. NMR data consistent with Nicolaou et al., J. Am. Chem. Soc. 114:3127 (1992) and C. W. Hummel, Ph.D. Dissertation, University of California, San Diego (1993).

Fuente