98474-85-2

Upstream product

• 58014-92-9 (3aR,6S,6aS)-1,3-Dibenzyl-6-methyl-5-oxo-hexahydro-5λ⁴-thieno[3,4-d]imidazol-2-one 
• 56198-35-7 (3aS,6aR)-1,3-Dibenzyl-5-oxo-hexahydro-5λ⁴-thieno[3,4-d]imidazol-2-one 
• 58014-92-9 (3aR,6R,6aS)-1,3-Dibenzyl-6-methyl-5-oxo-hexahydro-5λ⁴-thieno[3,4-d]imidazol-2-one 
• 75-16-1 methylmagnesium bromide 
• 103621-13-2 (+/-)-(3aα,4α,6aα)-4-Chlorotetrahydro-1,3-bis(phenylmethyl)-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 56198-34-6 (3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one 
• 917-54-4 methyllithium 

Relevant academic research and scientific papers

Nucleophilic Displacements on an α-Chloro Thioether by Organocuprates: A Novel Synthesis of Desoxybiotin

Reactions of organometallic reagents with α-chloro thioether 2, which is readily prepared from thienoimidazolone 1, have been investigated as an approach to the synthesis of biotin (10).Methyllithium and methylmagnesium bromide attack exclusively from the less hindered exo face, affording 4, while lithium dimethylcuprate attacks from the endo face with inversion of configuration, affording 5.Lithium dipentylcuprate affords predominantly exo isomer 6, while halide-free lithium methylpentylcuprate affords predominantly endo isomer 7.Debenzylation of 7 yields desoxybiotin (9) which can be microbially oxidized to biotin (10).Alternatively, 2 was hydrolyzed and oxidized to thiolactone 13, a known precursor of biotin.

300 MHZ (1)H NMR SPECTRA AND CONFORMATIONS OF BIOTIN AND RELATED HEXAHYDROTHIENOIMIDAZOLONE DERIVATIVES

(1)H NMR spectra of biotin and four related hexahydrothienoimidazolones in which the endo pentanoate side chain of biotin is replaced by another endo or exo substituent, and the urea nitrogen atoms are substituted with benzyl groups, have been obtained at