1408237-19-3

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 263253-11-8 (2R,4S)-hex-5-ene-2,4-diol 
• 374749-82-3 (1S,3S)-1'-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)butane-1,3-diol 
• 1205666-47-2 (S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-hydroxypent-4-en-1-one 
• 1408237-16-0 (5R,7S)-2,2,5,10,10-pentamethyl-3,3,9,9-tetraphenyl-7-vinyl-4,8-dioxa-3,9-disilaundecane 
• 1408237-17-1 (-)-(S)-3-hydroxypent-4-enoic acid methoxymethylamide 
• 1408237-18-2 (S)-4-hydroxyhex-5-en-2-one 
• 400710-04-5 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 64482-42-4 (-)-(S)-4-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-4-hydroxybutan-2-one 

Downstream Products

• 1408237-21-7 (2R,4S)-4-[(tert-butyldiphenylsilyl)oxy]hex-5-en-2-yl (S)-4-[(tert-butyldiphenylsilyl)oxy]hex-5-enoate 

Relevant academic research and scientific papers

Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-epi-Stagonolide C Employing Chiral Hexane-1,2,3,5-tetraol Derivatives as Building Blocks

An organocatalytic approach to the synthesis of (2R,3S)-hexane-1,2,3,5-tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline-catalyzed intermolecular aldol reaction between acetone and d-glyceraldehyde acetonide. The synthetic utility of the intermediates was demonstrated by their transformation into the title hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols.

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.