83541-80-4

Upstream product

• 67-56-1 methanol 
• 157020-40-1 -(3,6,7,8,9,10-Hexahydro-10-oxo-2H-thiecin-3-yl)-(phenylmethyl)carbamoyl azide 
• 55183-45-4 hex-5-in-carboxyl chloride 
• 78841-16-4 (1S,4R,10R,13R)-2-Benzyl-3-oxa-12-thia-2,9-diaza-tricyclo[8.3.0.0^4,13]tridecan-8-one 
• 608-16-2 biotin methyl ester 
• 58-85-5 biotin 
• 122224-36-6 1-N-(4,4'-dimethoxytrithyl)-D(+)-biotin methyl ester 
• 1340499-01-5 methyl 5-((3aS,4S,6aR)-3-benzyl-1-(bis(4-methoxyphenyl)-(phenyl)methyl)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate 
• 83541-73-5 (Z)-(R)-5-Oxo-3,4,5,6,7,8-hexahydro-2H-[1,4]thiazecine-3-carboxylic acid methyl ester 
• 78271-02-0 C₁₆H₂₀N₂O₂S 
• 83541-75-7 (Z)-(R)-5-Oxo-3,4,5,6,7,8-hexahydro-2H-[1,4]thiazecine-3-carbaldehyde 
• 83486-94-6 (R)-2-Hex-5-ynoylamino-3-((R)-2-hex-5-ynoylamino-2-methoxycarbonyl-ethyldisulfanyl)-propionic acid methyl ester 
• 83541-78-0 Benzyl-((1R,7R,8R,11S)-7-hydroxy-3-oxo-9-thia-2-aza-bicyclo[6.2.1]undec-11-yl)-carbamic acid methyl ester 
• 83486-95-7 (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-hydroxy-pentanoic acid 

Downstream Products

• 58-85-5 biotin 

Relevant academic research and scientific papers

Selective N-acylation and N-alkylation of biotin

Simple and efficient methodology is presented for the selective acylation and alkylation of biotin at its 3′-nitrogen.

Novel Enantioselective Syntheses of (+)-Biotin

Two conceptually attractive enantioselective syntheses of (+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide.The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of (+)-biotin 16a and 17a.The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b.Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.