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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2304199Generated: October 31, 2026

Tetrabutylammonium Fluoride → 1alpha,3beta-dihydroxy-20(S)-(4-ethyl-4-hydroxyhexylthio)pregna-5,7,16-triene

https://huagongshe.com/reaction/2304199

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant1alpha-(tert-butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(4-ethyl-4-hydroxyhexylthio)pregna-5,7,16-trieneHCID 12019518—
SolventTetrahydrofuranHCID 8028—
Product1alpha,3beta-dihydroxy-20(S)-(4-ethyl-4-hydroxyhexylthio)pregna-5,7,16-trieneHCID 1201952479.6%

Reaction Steps

Under the same conditions as in Example 9, the crude 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-(4-ethyl-4-hydroxyhexylthio)pregna-5,7,16-triene (71.4 mg) obtained in Example 8, tetrahydrofuran (2 ml) and 1M tetra-n-butyl-ammonium fluoride solution in tetrahydrofuran (2 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane:ethanol=7:1, developed once) to give the title compound as a colorless oil (45.8 mg, 67%, 2 steps).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06433200B1
Source datasetuspto-grants-2002_08
ORD IDord-a3220791fbc9400c9be97c85ccb141ac
Source noteuspto-grants-2002_08