HuagongsheHuagongshe Chemistry Print Report · For research reference only
m-Chloroperbenzoic acid → 5-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-((2-methyloxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | 5-chloro-4-(4-ethylbenzyl)-2-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(2-methylallyl)tetrahydro-2H-pyran-2-yl)phenol | HCID 68792676 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-((2-methyloxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)phenol | HCID 86621849 | 77.5% |
Reaction Steps
To a solution of 25 (52 mg, 63 μmol) in anhydrous DCM (1 mL) was added 3-chlorobenzoperoxoic acid (21 mg, 95 μmol, 1.2 equiv). The reaction was stirred overnight, directly loaded onto a preparatory TLC plate, and eluted with 15% EtOAc in petroleum ether to give 50 (41 mg, 77% yield). LC/MS m/z 862 (M+Na).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07795228B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-c96feda6099445988437514452871d1a |
| Source note | uspto-grants-2010_09 |