Reacción #74504

ord-219346c1a17348648b2e7be5de7a1262

Ecuación de reacción

OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1
compound 2
OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1
2,3,4,6-tetra-O-benzyl-D-glucopyranose
CC(C)[Si](OCc1cc(Br)c(Cl)cc1Cl)(C(C)C)C(C)C
(5-bromo-2,4-dichlorobenzyloxy)triisopropylsilane
CC(C)[Si](OCc1cc(Br)c(Cl)cc1Cl)(C(C)C)C(C)C
compound 82
CC(C)[Si](OCc1cc(Br)c(Cl)cc1Cl)(C(C)C)C(C)C
(5-bromo-2,4-dichlorobenzyloxy)triisopropylsilane
OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1
2,3,4,6-tetra-O-benzyl-D-glucopyranose
→
OCc1cc(C2O[C@H](COCc3ccccc3)[C@@H](OCc3ccccc3)[C@H](OCc3ccccc3)[C@H]2OCc2ccccc2)c(Cl)cc1Cl
title compound
OCc1cc(C2O[C@H](COCc3ccccc3)[C@@H](OCc3ccccc3)[C@H](OCc3ccccc3)[C@H]2OCc2ccccc2)c(Cl)cc1Cl
(2,4-Dichloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol

Reactantes

OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1
compound 2
OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1
2,3,4,6-tetra-O-benzyl-D-glucopyranose
CC(C)[Si](OCc1cc(Br)c(Cl)cc1Cl)(C(C)C)C(C)C
(5-bromo-2,4-dichlorobenzyloxy)triisopropylsilane
CC(C)[Si](OCc1cc(Br)c(Cl)cc1Cl)(C(C)C)C(C)C
compound 82
CC(C)[Si](OCc1cc(Br)c(Cl)cc1Cl)(C(C)C)C(C)C
(5-bromo-2,4-dichlorobenzyloxy)triisopropylsilane
OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1
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-2,4-dichlorobenzyloxy)triisopropylsilane (compound 82, 41.7 g, 101 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (compound 2, 45.4 g, 84.0 mmol) were converted to title compound (47.6 g, 81%, ca. 8:1 mixture of anomers (13:0) as a white solid.

Fuente

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