161985-39-3

Upstream product

• 132489-33-9 (S)-2-benzyloxy-3-pentanone 
• 78-84-2 isobutyraldehyde 
• 160666-92-2 (S)-2-benzoyloxypentan-3-one 
• 93-97-0 benzoic acid anhydride 
• 125948-63-2 (S)-2-hydroxypentan-⁽³⁾-one 

Downstream Products

• 161985-49-5 (3S,4S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3-methyl-5-methylene-octan-2-one 
• 161985-50-8 (3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one 
• 167842-02-6 (2S,4R,5R)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptan-3-one 
• 888488-17-3 (3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one 
• 888488-07-1 (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione 
• 888488-39-9 (2S,4R,5R,6R,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-triethylsilyloxy-4,6,8-trimethylnon-3-one 
• 888488-42-4 (2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one 

Relevant academic research and scientific papers

A retro-Claisen approach to dolabriferol

The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone

Polyketide synthesis using the boron-mediated, anti-aldol reactions of lactate-derived ketones: Total synthesis of (-)-ACRL toxin IIIB

The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reag

Stereocontrolled Aldol Additions to α-Methylene-β-Alkoxy Aldehydes: Application to the Synthesis of a C13-C25 Segment of Bafilomycin A1.

A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C16 and acetonide hydrolysis, gives the C13-C25 segment 6 of bafilomycin A1.

Studies in polypropionate synthesis: High π-face selectivity in Syn and Anti aldol reactions of chiral boron enolates of lactate-derived ketones

Use of (c)Hex2Bcl/Me2NEt in the aldol reactions of the α'-benzoyloxy ketone 7 with aldehydes leads to high stereoselectivity (97-95.5% ds) for the crystalline anti adducts 11. Under similar conditions, the corresponding benzyl ether 6 favours formation of the syn adducts 9.