HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2206797Generated: October 31, 2026
Boron Trichloride → (2S,3R,4R,5S,6R)-2-(4-Chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-3,4,5-triol
https://huagongshe.com/reaction/2206797
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Boron Trichloride | HCID 25135 | — |
| Reactant | 6-(2-Chloro-5-((2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-thiopyran-2-yl)benzyl)-2,3-dihydrobenzo[b][1,4]dioxine | HCID 71078590 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2S,3R,4R,5S,6R)-2-(4-Chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-3,4,5-triol | HCID 71110651 | 12% |
Reaction Steps
6-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl) tetrahydro-2H-thiopyran-2-yl)benzyl)-2,3-dihydrobenzo[b][1,4]dioxine (126, 204 mg, 0.26 mmol) in dichloromethane (5 mL) reacted with BCl3 (1.5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 h. After quenching the reaction with methanol, solvent was evaporated under a reduced pressure. Purification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient) provided the title compound (E047, 13 mg, 12% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09371303B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-2d0317ae99e749d4b8eb426c0e34b82b |
|---|
| Source note | uspto-grants-2016_06 |
|---|
