HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → (2,4-Dichloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose | HCID 10940502 | — |
| Reactant | (5-Bromo-2,4-dichlorobenzyloxy)triisopropylsilane | HCID 53329583 | — |
| Product | (2,4-Dichloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol | HCID 53329750 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08541380B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-219346c1a17348648b2e7be5de7a1262 |
| Source note | uspto-grants-2013_09 |