56198-32-4

Upstream product

• 28092-62-8 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 56198-73-3 dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate 

Downstream Products

• 350228-40-9 1,3-dibenzyl-4,5-cis-bis(chloromethyl)-2-imidazolidone 
• 95790-94-6 Acetic acid (4S,5R)-5-acetoxymethyl-1,3-dibenzyl-2-oxo-imidazolidin-4-ylmethyl ester 
• 95790-95-7 Acetic acid (4S,5R)-1,3-dibenzyl-5-hydroxymethyl-2-oxo-imidazolidin-4-ylmethyl ester 
• 28092-62-8 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 56198-34-6 (3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one 

Relevant academic research and scientific papers

Synthesis of new biotin derivatives

It is now established that the formation of C-S bonds during the conversion of dethiobiotin into biotin involves intermediate carbon radicals. To examine the behavior of dethiobiotin analogs that could lead to allylic and α-epoxyradicals, we have synthesized 4,5-dehydrodethiobiotins and the corresponding epoxides and 5,6-dehydrodethiobiotins. All these compounds have been labelled with 14C on the carboxyl group.

Chemoenzymatic synthesis of d-biotin intermediate lactone via lipase-catalyzed desymmetrization of meso diols

A chemoenzymatic methodology for the asymmetric synthesis of d-biotin intermediate lactone ((3aS, 6aR)-tetrahydro-1,3-dibenzylhexahydro-1H-Furo[3,4-d] imidazole-2,4-dione) 1 has been demonstrated. The key step of the synthetic routes is Lipozyme RM IM catalyzed desymmetrization of meso-diols 3. The highest enantiomeric excess (e.e. > 98%) and yield (>90%) of the product was achieved with Lipozyme RM IM in Dioxane/Toluene (1:3, v/v) at 35 C. Furthermore, Lipozyme RM IM showed an excellent operational stability, retaining above 80% of the initial activity after 10 cycles of reaction. d-Biotin intermediate lactone 1 was obtained subsequently by Jones oxidation, basic hydrolysis and lactonization.