HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroform → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[5-[4-(2-aminoethyl)benzyl]-2-(benzyloxy)-4-methylphenyl]-D-glucitol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Trifluoroacetate | HCID 84468 | — |
| Reactant | (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-[4-[2-(tritylamino)ethyl]benzyl]phenyl]-D-glucitol | HCID 86638440 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[5-[4-(2-aminoethyl)benzyl]-2-(benzyloxy)-4-methylphenyl]-D-glucitol | HCID 67303921 | 103.1% |
Reaction Steps
To a chloroform solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-[4-[2-(tritylamino)ethyl]benzyl]phenyl]-D-glucitol (0.402 g, 0.336 mmol) was added at room temperature trifluoroacetate (0.5 mL), and the mixture was stirred for 3 hours at the same temperature. To the reaction solution was added ethanol and then the solvent was evaporated under reduced pressure. Thus obtained residue was purified with NH type silica gel column chromatography (hexane:ethyl acetate=4:6, chloroform:methanol=20:1) to obtain the title compound (0.296 g, quant.) as a colorless oily compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07973012B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-efedbf8244ce459eba960521bc053ea1 |
| Source note | uspto-grants-2011_07 |