214683-74-6

Basic information

• Product Name: (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecan-1-ol
• Synonyms: (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecan-1-ol
• CAS NO: 214683-74-6
• Molecular Weight: 566.984
• Mol File: 214683-74-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecan-1-ol(214683-74-6)
• EPA Substance Registry System: (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecan-1-ol(214683-74-6)

Safety Data

• Hazardous Substances Data: 214683-74-6(Hazardous Substances Data)

Upstream product

• 130645-87-3 (7R,8S,10S)-10-Benzyloxy-7-(tert-butyldimethylsilyloxymethyl)-8-dimethyl(phenyl)silylhenicosane 
• 26186-02-7 tridec-1-yne 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 17156-64-8 (dimethylphenylsilyl)acetylene 
• 130625-73-9 (Dimethyl-phenyl-silanyl)-propynoic acid 
• 130645-86-2 (E)-1-dimethyl(phenyl)silyltridec-1-ene 
• 214683-72-4 (Z)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hexyl-hexadec-4-en-1-ol 
• 130625-77-3 ({(Z)-(S)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-heptyl]-tetradec-2-enyl}-dimethyl-silanyl)-benzene 
• 130625-75-1 (Z)-3-(Dimethyl-phenyl-silanyl)-hexadec-4-enoic acid benzyl ester 
• 130625-78-4 (7R,8S,10S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-8-(dimethyl-phenyl-silanyl)-henicosan-10-ol 
• 130625-76-2 (Z)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hexyl-hexadec-4-enoic acid benzyl ester 
• 130696-99-0 (S)-1-[(Z)-3-(Dimethyl-phenyl-silanyl)-acryloyl]-5-trityloxymethyl-pyrrolidin-2-one 
• 214683-66-6 ({(E)-(S)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-heptyl]-tetradec-2-enyl}-dimethyl-silanyl)-benzene 
• 214683-65-5 (E)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hexyl-hexadec-4-enoic acid tert-butyl ester 

Downstream Products

• 108051-94-1 N-[(phenylmethoxy)carbonyl]-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 
• 134453-14-8 (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one 
• 104872-04-0 Orlistat 
• 130625-79-5 (2R,3S,5S)-5-Benzyloxy-3-(dimethyl-phenyl-silanyl)-2-hexyl-hexadecanoic acid 
• 134453-13-7 (2S,3S,5S)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid 
• 104871-99-0 (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one 

Relevant articles and documents

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.