HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | (4R,4aS,7R,7aR)-7-methoxy-2,2-dimethyl-4-vinyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one | HCID 49871274 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one | HCID 67241097 | 94.4% |
Reaction Steps
10 ml of TFA are added dropwise, at 0° C., to a 100 ml round-bottomed flask containing 1.0 g of 17 (4.38 mmol), 10 ml of water and 14 ml of THF. The medium is left to return to AT and stirred overnight. The medium is then concentrated at reduced pressure, at AT, and 50 ml of water are added, and the mixture is frozen and lyophilized. The lyophilizate is made into a paste in heptane, in the presence of a minimum amount of methanol, after the solvents have been evaporated off. 778 mg of expected product 18 (white solid) are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07994162B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-61cd48c5046b47a29e1c664c3d7b3d71 |
| Source note | uspto-grants-2011_08 |