Synthesis of (+)-Biotin
Shen Run-pu
Abstract
Shen Run-pu
Abstract
(+)-Biotin was synthesized from (3aS,4S,6aR)-1,3-dibenzyl-6-(3-methoxypropyl)-tetrahydrothieno[3,4-d]imidazol-2-one by chlorination with concentrated hydrochloride to give (3aR,8aS,8bS)-1,3-dibenzyl-2-oxodecahydroimadazo[4,5-c]thieno[1,2-a]thiolium chloride, which was subjected to condensation and ring opening, hydrolysis and decarboxylation with an overall yield of about 73%.
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(+)-Biotin was synthesized from (3aS,4S,6aR)-1,3-dibenzyl-6-(3-methoxypropyl)-tetrahydrothieno[3,4-d]imidazol-2-one by chlorination with concentrated hydrochloride to give (3aR,8aS,8bS)-1,3-dibenzyl-2-oxodecahydroimadazo[4,5-c]thieno[1,2-a]thiolium chloride, which was subjected to condensation and ring opening, hydrolysis and decarboxylation with an overall yield of about 73%.
Key concepts: Chemistry, Yield (engineering), Decarboxylation, Biotin, Hydrochloride, Chloride, Hydrolysis, Condensation