139623-16-8

Basic information

• Product Name: 1-Tetradecanol, 3-(phenylmethoxy)-, (R)-
• Synonyms: (R)-3-Benzyloxy-1-tetradecanol;1-Tetradecanol,3-(phenylmethoxy)-,(R);(R)-3-benzyloxy-1-hydroxytetradecane;(R)-3-(Benzyloxy)tetradecan-1-ol
• CAS NO: 139623-16-8
• Molecular Formula: C21H36O2
• Molecular Weight: 320.50900
• Mol File: 139623-16-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-Tetradecanol, 3-(phenylmethoxy)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Tetradecanol, 3-(phenylmethoxy)-, (R)-(139623-16-8)
• EPA Substance Registry System: 1-Tetradecanol, 3-(phenylmethoxy)-, (R)-(139623-16-8)

Safety Data

• Hazardous Substances Data: 139623-16-8(Hazardous Substances Data)

Upstream product

• 139623-14-6 (R)-3-hydroxy-1-trityloxytetradecane 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 1026544-99-9 (R)-1-<(tert-Butyldiphenylsilyl)oxy>-3-hydroxytetradecane 
• 112-29-8 1-bromo dodecane 
• 148407-40-3 (2R,3R)-3-undecyloxirane-2-methanol 
• 79413-94-8 (2S,4S)-2-Phenyl-4-tosyloxymethyl-1,3-dioxan 
• 139623-13-5 (R)-1,3-dihydroxytetradecane 
• 17049-50-2 n-decyl magnesium bromide 
• 103773-79-1 [(2S,4S)-2-phenyl-1,3-dioxan-4-yl]methanol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 354567-18-3 (4R)-2-phenyl-4-undecyl-1,3-dioxane 
• 153011-62-2 (R)-3-(Benzyloxy)-1-<(tert-butyldiphenylsilyl)oxy>tetradecane 
• 139623-15-7 (R)-3-benzyloxy-1-trityloxytetradecane 

Downstream Products

• 114264-05-0 (3S,4S)-4-((R)-2(benzyloxy)tridecyl)-3-hexyl-2-oxetanone 
• 114299-20-6 (2S,3S,5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid 
• 152906-10-0 Methyl (3S,5R)-5-(benzyloxy)-3-hydroxydecanoate 
• 152906-09-7 (4S,6R)-6-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-1-heptadecane 
• 152906-21-3 Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate 
• 152906-11-1 Phenyl (3S,5R)-5-(benzyloxy)-3-hydroxydecanethioate 
• 87357-67-3 (R)-3-benzyloxytetradecanoic acid 
• 132791-96-9 allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside 
• 139623-11-3 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate 
• 132828-14-9 2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl dibenzyl phosphate 
• 132791-95-8 allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranoside 
• 139623-09-9 Allyl 4,6-O-<(3R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranoside 
• 132832-52-1 Allyl 2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 
• 132791-94-7 Allyl 2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranoside 

Relevant articles and documents

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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.