449729-48-0

Upstream product

• 151415-05-3 N-(Phenylmethyl)-3(R)-bromo-2(R)-(carbomethoxybutyl)tetrahydrothiophene-4(S)-carbamoyl azide 
• 1026976-17-9 C₁₈H₂₃BrClNO₃S 
• 151415-02-0 cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester 
• 1027086-34-5 cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid 
• 161458-88-4 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester 
• 161458-89-5 <2S-(2α,3β,4α)>-3-Bromotetrahydro-4-<(phenylmethyl)amino>-2-thiophenepentanoic acid methyl ester 
• 151415-03-1 5-<3(R)-Bromo-4(S)-<(methoxycarbonyl)amino>tetrahydrothiophen-2(R)-yl>pentanoic acid methyl ester 
• 50889-29-7 (5-carboxypentyl)triphenylphosphonium bromide 
• 1025879-11-1 (2R,4R)-4-((S)-6-Carboxy-2-oxo-1-trimethylsilanyloxy-hexyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 449729-44-6 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-methoxycarbonyloxy-6-oxoheptanoic acid methyl ester 
• 449729-39-9 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid 
• 449729-42-4 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester 
• 100-52-7 benzaldehyde 
• 449729-46-8 5-[(3S,4R)-4-(1-Benzyl-ureido)-3-methoxycarbonyloxy-dihydro-thiophen-(2E)-ylidene]-pentanoic acid methyl ester 

Downstream Products

• 151526-81-7 <3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester 
• 608-16-2 biotin methyl ester 
• 58-85-5 biotin 

Relevant academic research and scientific papers

A highly stereocontrolled total synthesis of (+)-biotin from L-cysteine

(+)-Biotin was synthesized in 11 steps and in 25% overall yield from readily accessible L-cysteine through a Lewis base-catalyzed highly diastereoselective cyanosilylation of (2R,4R)-N-Boc-2-phenylthiazolidine-4-carbaldehyde 2 and a ring closure of a cis-allylic carbonate 5b utilizing a palladium-catalyzed intramolecular allylic amination.

A Novel Enantioselective Synthesis of (+)-Biotin

A conceptually simple enantioselective 14-step synthesis of (+)-biotin from L-cysteine is reported based upon an intramolecular 1,3-dipolar cyclodaddition sequence involving (i) elimination of bromide 8 to the endocyclic thioenol ether 9, (ii) thermolysis of the ene carbamoyl azide 9 to the exocyclic thioenol ether 10.Both the synthesis of 8 and the final transformation of 10 into (+)-biotin are based upon literature precedents.