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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1670414Generated: October 26, 2026

Water → (3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one

https://huagongshe.com/reaction/1670414

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTrifluoroacetic acidHCID 6422—
Reactant(4R,4aS,7R,7aR)-7-methoxy-2,2-dimethyl-4-vinyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-oneHCID 49871274—
SolventTetrahydrofuranHCID 8028—
Product(3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-oneHCID 6724109794.4%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07994162B2
Source datasetuspto-grants-2011_08
ORD IDord-61cd48c5046b47a29e1c664c3d7b3d71
Source noteuspto-grants-2011_08