Reacción #74508

ord-2c3a65c066ad4c4fa274a5b279ee8e5d

Ecuación de reacción

OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1

compound 2

2,3,4,6-tetra-O-benzyl-D-glucopyranose

COc1cc(Cl)c(CO[Si](C(C)C)(C(C)C)C(C)C)cc1Br

(5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane

compound 89

(5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane

2,3,4,6-tetra-O-benzyl-D-glucopyranose

→

COc1cc(Cl)c(CO)cc1C1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1

title compound

(2-Chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol

Reactantes

compound 2

2,3,4,6-tetra-O-benzyl-D-glucopyranose

(5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane

compound 89

(5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane

2,3,4,6-tetra-O-benzyl-D-glucopyranose

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas

See reaction.notes.procedure_details.

Procedimiento

With similar method described in Step 3 of Example 92, (5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane (compound 89, 27.2 g, 66.7 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (compound 2, 30.0 g, 55.6 mmol) were converted to title compound (22.6 g, 59%, ca. 8:1 mixture of anomers (13:0) as a white solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08541380B2uspto-grants-2013_09