134453-14-8

Basic information

• Product Name: (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one
• Synonyms: (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one
• CAS NO: 134453-14-8
• Molecular Weight: 444.698
• Mol File: 134453-14-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one(134453-14-8)
• EPA Substance Registry System: (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one(134453-14-8)

Safety Data

• Hazardous Substances Data: 134453-14-8(Hazardous Substances Data)

Upstream product

• 26186-02-7 tridec-1-yne 
• 138650-27-8 (S)-3-benzyloxytetradecanal 
• 134360-68-2 (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-(benzyloxy)hexadecanoate 
• 134360-69-3 (2S,3S,5S)-benzyl 2-hexyl-3-hydroxy-5-(benzyloxy)hexadecanoate 
• 134453-12-6 (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate 
• 134360-67-1 (3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-2-one 
• 214683-69-9 Dimethyl-phenyl-tridec-1-ynyl-silane 
• 638-45-9 1-Iodohexane 
• 130645-87-3 (7R,8S,10S)-10-Benzyloxy-7-(tert-butyldimethylsilyloxymethyl)-8-dimethyl(phenyl)silylhenicosane 
• 130625-79-5 (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid 
• 130625-76-2 (Z)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hexyl-hexadec-4-enoic acid benzyl ester 
• 130625-78-4 (7R,8S,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-8-(dimethyl-phenyl-silanyl)-henicosan-10-ol 
• 130625-75-1 (Z)-3-(Dimethyl-phenyl-silanyl)-hexadec-4-enoic acid benzyl ester 
• 130625-77-3 ({(Z)-(S)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-heptyl]-tetradec-2-enyl}-dimethyl-silanyl)-benzene 

Downstream Products

• 104872-04-0 Orlistat 
• 108051-94-1 N-[(phenylmethoxy)carbonyl]-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 
• 104871-99-0 (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one 

Relevant articles and documents

Asymmetric synthesis of (-)-tetrahydrolipstatin from a β-hydroxy- δ-oxo sulfoxide

An asymmetric synthesis of (-)-tetrahydrolipstatin is described. A palladium-catalyzed regioselective oxidation of an alkene to a ketone, highly diastereoselective reduction of a β-hydroxy ketone, selective oxidation of a diol, and modular synthesis are the key features of the synthesis. Georg Thieme Verlag Stuttgart.

Asymmetric synthesis of tetrahydrolipstatin and valilactone

The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] and β-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to β-substituted and α,β-disubstituted β-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetrahydrolipstatin and valilactone.

Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of (-)-tetrahydrolipstatin using the alkylation of a β-silyl ester and the hydroboration of an allylsilane

Conjugate addition of bis(Z-tridec-1-enyl)cuprate Z-10 to (5S)-1-[(Z)-3′-dimethyl(phenyl)silylprop-2-enoyl]-5-(trityloxymethyl) pyrrolidin-2-one Z-6 gave the 3A-imide Z-12. Subsequent enolate n-hexylation of the benzyl ester Z-13a derived from this imide gave the 2R,3S-ester Z-14a. Reduction of the ester group and protection of the alcohol as its TBDMS group gave the allylsilane (Z)(7 R,8S)-7-(tert-butyldimethylsilyloxymethyl)-8-dimethyl(phenyl)silylhenicos-9-ene Z-15. Hydroboration-oxidation gave the 7R,8S,10S-alcohol 16. Protection of the C-10 hydroxy as its benzyl ether, removal of the silyl protecting group and oxidation gave (2R,3S,5S)-5-benzyloxy-3-dimethyl(phenyl)silyl-2-hexylhexadecanoic acid 19. Silyl-to-hydroxy conversion, β-lactone formation, and hydrogenolysis gave the known alcohol (3S,4S)-3-hexyl-4-[(S)-2′-hydroxytridecyl]oxetan-2-one 22, from which tetrahydrolipstatin 1 was prepared by a conventional esterification. Each of the stereochemistry determining steps, 4 → Z-6, 7 → E-8, E-8 → Z-9, Z-6 + Z-10 → Z-12, Z-13a → Z-14a and Z-15 → 16, took place with a remarkably high level of open-chain stereocontrol.