2009Chinese Journal of PharmaceuticalsRequires access

Synthesis of (+)-Biotin

Shen Run-pu

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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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What this paper is about

(+)-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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Available 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%.

Key concepts: Chemistry, Yield (engineering), Decarboxylation, Biotin, Hydrochloride, Chloride, Hydrolysis, Condensation

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