Réaction #74502

ord-340547e3c1454fe5ae5d9e5a02207d7e

Équation de réaction

CC(C)[Si](OCc1cc(Br)cc2ccccc12)(C(C)C)C(C)C
((3-bromonaphthalen-1-yl)methoxy)triisopropylsilane
CC(C)[Si](OCc1cc(Br)cc2ccccc12)(C(C)C)C(C)C
compound 76
CC(C)[Si](OCc1cc(Br)cc2ccccc12)(C(C)C)C(C)C
((3-bromonaphthalen-1-yl)methoxy)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)cc2ccccc12
title compound
OCc1cc(C2O[C@H](COCc3ccccc3)[C@@H](OCc3ccccc3)[C@H](OCc3ccccc3)[C@H]2OCc2ccccc2)cc2ccccc12
(3-((3S,4R,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)naphthalen-1-yl)methanol

Réactifs

CC(C)[Si](OCc1cc(Br)cc2ccccc12)(C(C)C)C(C)C
((3-bromonaphthalen-1-yl)methoxy)triisopropylsilane
CC(C)[Si](OCc1cc(Br)cc2ccccc12)(C(C)C)C(C)C
compound 76
CC(C)[Si](OCc1cc(Br)cc2ccccc12)(C(C)C)C(C)C
((3-bromonaphthalen-1-yl)methoxy)triisopropylsilane
OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1
2,3,4,6-tetra-O-benzyl-D-glucopyranose

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

With similar method described in Step 3 of Example 92, ((3-bromonaphthalen-1-yl)methoxy)triisopropylsilane (compound 76, 18.0 g, 45.6 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (2, 20.5 g, 38.0 mmol) were converted to title compound (23.3 g, 90%, ca. 2:1 mixture of anomers (13:0) as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08541380B2uspto-grants-2013_09