- Chemical Name:Vitamin D
- CAS No.:1406-16-2
- Molecular Formula:C27H44O
- Molecular Weight:384.63766
- Hs Code.:
- Mol file:1406-16-2.mol
Synonyms:CCRIS 5813; Activated ergosterol
Synonyms:CCRIS 5813; Activated ergosterol
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The research focuses on the chemical transformation of 5,6-trans-vitamin D conjugated triene system into that of isovitamin D under nucleophilic conditions. The study reports the first instance of this conversion, which involves a carbanionic intermediate produced by n-butyl-lithium. The reaction is characterized as a novel SN2' reaction where a trialkylsilyloxide anion is substituted by a 1-butyl anion. The purpose of the research was to explore the chemical and biological interest in the transformations of vitamin D derivatives, specifically the conversion of 5,6-e-vitamin D (2) into isovitamin D (3). The key chemicals used in this process include 1,2-dimethylbutyl-lithium (n-butyl-lithium), tetrahydrofuran (THF) as a solvent, and bis-m-butyldimethylsilyl (TBDMS) ether as a protecting group for the la-hydroxy group of vitamin D. The conclusion of the research is that the reaction constitutes a successful conversion of the 5,6-trans-vitamin D triene system into that of isovitamin D under nucleophilic conditions, involving the addition of butyl anion at C-1 to give a pentadienyl carbanion, followed by expulsion of the silyloxide. The study also notes that methyl-lithium reacts similarly and that further exploration of the reaction with other types of nucleophiles is underway.