334976-33-9

Upstream product

• 4541-14-4 4-benzyloxy-butan-1-ol 
• 100-39-0 benzyl bromide 
• 5470-84-8 4-benzyloxybutanal 
• 334976-32-8 acetic acid 1-(3-benzyloxy-propyl)-prop-2-ynyl ester 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 334976-37-3 (S)-6-(benzyloxy)hex-1-en-3-ol 

Downstream Products

• 1408237-20-6 (S)-4-[(tert-butyldiphenylsilyl)oxy]hex-5-enoic acid 
• 1408237-21-7 (2R,4S)-4-[(tert-butyldiphenylsilyl)oxy]hex-5-en-2-yl (S)-4-[(tert-butyldiphenylsilyl)oxy]hex-5-enoate 
• 334976-34-0 (S)-4-(tert-butyldiphenylsilyl)oxy-5-hexenyl methanesulfonate 
• 334976-35-1 (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal 
• 334976-46-4 (S)-4-(tert-butyldiphenylsilyl)oxy-5-hexen-1-ol 

Relevant academic research and scientific papers

Stereoselective total synthesis of stagonolide-C

The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis.

A concise enantioselective synthesis of antimalarial febrifugine alkaloids.

Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.