HuagongsheHuagongshe Chemistry Print Report · For research reference only
P-Cresol → 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | P-Cresol | HCID 2879 | — |
| Reactant | ((2R,3S,4S,5R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl)methyl acetate | HCID 2729838 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Product | 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside | HCID 54141638 | 40% |
Reaction Steps
According to scheme XIV, the coupling of penta-O-acetyl-D-galactopyranose (36 g, 92 mmoles) with p-cresol (30 g, 280 mmoles) is carried out by fusion in the presence of anhydrous ZnCl2 (1.8 g) at 160° C. for 30 minutes, according Helferich technique. After cooling, a chromatography on a column of 60H silica (solvent:hexane-ethyl acetate: 90/10-v/v) is directly performed on the mixture and gives 15 g, yield=40% of 4-methylphenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside, which crystallises in ethanol. Its analytical characteristics are identical as the one described before.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05561119 |
| Source dataset | uspto-grants-1996_10 |
| ORD ID | ord-cf4cbe1b15964af294e3fcd1df036bad |
| Source note | uspto-grants-1996_10 |