HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Alcohol → HCID 69980896, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triethylsilyl trifluoromethanesulphonate | HCID 2733308 | — |
| Reactant | HCID 69350255 | HCID 69350255 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69980896 | HCID 69980896 | 91% |
Reaction Steps
1.62 mL (3 eq.) of benzyl alcohol and 130 μL (0.1 eq.) of TESOTf are added to 3.07 g (1 eq.) of 2-O-acetyl-3-O-allyl-4,6-di-O-benzyl-α-D-gluco-pyranosyl trichloroacetimidate (M=586.5) in 25 mL of dichloromethane at 0° C. in the presence of 2.5 g of 4 Å molecular seives. After 1 hour of reaction at 0° C., the medium is neutralised with triethylamine, filtered and concentrated. Purification over silica gel [flash; eluent: toluene/ethyl acetate (98/2; v/v)] enables isolating 2.52 g of benzyl 2-O-acetyl-3-O-allyl-4,6-di-O-benzyl-β-D-glucopyranoside (M=532).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06951934B2 |
| Source dataset | uspto-grants-2005_10 |
| ORD ID | ord-c38cde88e21a4a459d19713b19472f88 |
| Source note | uspto-grants-2005_10 |