112763-97-0

Upstream product

• 114264-01-6 methyl (R)-3-(benzyloxy)tetradecanoate 
• 139623-16-8 (R)-3-benzyloxy-1-hydroxytetradecane 
• 112-54-9 Dodecanal 
• 100-39-0 benzyl bromide 
• 1026544-99-9 (R)-1-<(tert-Butyldiphenylsilyl)oxy>-3-hydroxytetradecane 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 77889-04-4 (R)-(-)-1-tetradecyn-3-ol 
• 73501-40-3 tetradec-1-yn-3-one 
• 74794-26-6 (3R)-1-trimethylsilyl-tetradec-1-yn-3-ol 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 153011-62-2 (R)-3-(Benzyloxy)-1-<(tert-butyldiphenylsilyl)oxy>tetradecane 
• 76828-23-4 (4RS)-1-pentadecen-4-ol 
• 112-29-8 1-bromo dodecane 

Downstream Products

• 152906-11-1 Phenyl (3S,5R)-5-(benzyloxy)-3-hydroxydecanethioate 
• 114264-04-9 (1R,2S)-2-(dimethylamino)-1-phenylpropyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate 
• 161443-50-1 (3R,4S)-3-hexyl-3-trimethylsilyl-4-<(R)-2'-(benzyloxy)tridecyl>-2-oxetanone 
• 220583-64-2 Benzoic acid (1R,3S,4S,6R)-6-benzyloxy-3-hexyl-4-hydroxy-1-methyl-2-oxo-heptadecyl ester 
• 104871-99-0 (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one 
• 104801-96-9 (3S,4S,6R)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one 
• 112764-01-9 (3S,4S,6R)-4-(benzyloxy)-3-hexyl-3,4,5,6-tetrahydro-6-undecyl-2H-pyran-2-one 
• 112764-03-1 benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-hydroxyhexadecanoate 
• 112764-04-2 benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate 
• 112764-05-3 (S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester 
• 68711-33-1 (6R)-3-hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one 
• 125638-38-2 (3S,4R)-4-((R)-2-Benzyloxy-tridecyl)-3-hexyl-oxetan-2-one 
• 125638-36-0 (3R,4R)-4-((R)-2-Benzyloxy-tridecyl)-3-hexyl-oxetan-2-one 
• 125638-37-1 (3R,4S)-3-hexyl-4-<(R)-2'-(benzyloxy)tridecyl>-2-oxetanone 

Relevant academic research and scientific papers

Stereoselective synthesis of (-)-tetrahydrolipstatin via a radical cyclization based strategy

An efficient and flexible approach for the total synthesis of (-)-tetrahydrolipstatin is described. The main features of the synthetic strategy are a stereocontrolled radical cyclization and the successful utilization of commercially available S-malic acid.

Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin

Formula presented A [2+3] cycloaddition of camphor-derived oxazoline N-oxide to α,β-unsaturated ester afforded adduct 8. Tetrahydrolipstatin 1 was prepared from this compound in a nine-step sequence of reactions.

Total synthesis of (-)-tetrahydrolipstatin

The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain- extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91% ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38% overall yield.