HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose | HCID 10940502 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Acetic Anhydride | HCID 7918 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one | HCID 10907626 | 95% |
Reaction Steps
(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol (4) (2.00 g, 3.7 mmol, Senn Chemicals) was dissolved in solution of 12.0 mL DMSO and 8.0 mL Ac2O. After stirring for 12 h, the reaction was diluted with EtOAc, washed with H2O (1×), sat. NaHCO3 (1×), then dried (Na2SO4) and concentrated using high-vacuum to provide a syrup (1.89 g, 95%). LC/MS 100% (ELSD) tR=3.10 min, calcd for C34H34O6: 538.24, found 539.4 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07795228B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-26fafb295e9543acba3bb4dd4a9ba6fc |
| Source note | uspto-grants-2010_09 |