HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → (3-((3S,4R,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)naphthalen-1-yl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose | HCID 10940502 | — |
| Reactant | ((3-Bromonaphthalen-1-yl)methoxy)triisopropylsilane | HCID 59463745 | — |
| Product | (3-((3S,4R,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)naphthalen-1-yl)methanol | HCID 67287154 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08541380B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-340547e3c1454fe5ae5d9e5a02207d7e |
| Source note | uspto-grants-2013_09 |