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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1708817Generated: November 1, 2026

p-Toluenesulfonic acid → 1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde

https://huagongshe.com/reaction/1708817

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acidHCID 6101—
Reactant20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-dieneHCID 57254932—
SolventAcetoneHCID 180—
Product1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehydeHCID 8674583566.6%

Reaction Steps

In 10 ml of acetone was dissolved 110 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(tert-butyldimethylsilyl)oxy- 3β-(N,N-dimethylcarbamoyl)oxypregna-5,7diene, followed by addition of 10 mg of p-toluenesulfonic acid. The mixture was refluxed in an atmosphere of argon gas for 4 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 63 mg of 1α-(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05359055
Source datasetuspto-grants-1994_10
ORD IDord-9e752b8f0f44497f8c263365f493253d
Source noteuspto-grants-1994_10