150162-78-0

Basic information

• Product Name: (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one
• Synonyms: (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one
• CAS NO: 150162-78-0
• Molecular Weight: 404.59
• Mol File: 150162-78-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one(150162-78-0)
• EPA Substance Registry System: (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one(150162-78-0)

Safety Data

• Hazardous Substances Data: 150162-78-0(Hazardous Substances Data)

Upstream product

• 99274-32-5 2,4-O-benzylidene-D-threose 
• 88303-25-7 tetradecylmagnesium bromide 
• 303752-90-1 1,3-O-benzylidene-(D-arabino/L-xylo)-1,2,3,4-octadecanetetrol 

Downstream Products

• 117168-55-5 (2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol 
• 117168-65-7 (2R,3R,4S)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol 
• 150162-80-4 (2R,3S,4R)-1,3-O-benzylidene-2-(tert-butyldimethylsilyloxy)-4-methyloctadecane-1,3,4-triol 
• 150162-87-1 (2R,3S,4S)-1,3-O-benzylidene-2-(tert-butyldimethylsilyloxy)-4-methyloctadecane-1,3,4-triol 
• 150162-79-1 (2R,3S,4R)-1,3-O-benzylidene-4-methyloctadecane-1,2,3,4-tetrol 
• 150162-86-0 (2R,3S,4S)-1,3-O-benzylidene-4-methyloctadecane-1,2,3,4-tetrol 
• 167084-00-6 (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol 
• 160280-65-9 (2R,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl methanesulfonate 
• 117168-66-8 (2S,4R,5R)-4-[(R)-1-hydroxypentadecyl]-2-phenyl-1,3-dioxan-5-yl methanesulfonate 
• 117168-58-8 2-azido-1,3-O-benzylidene-D-ribo-1,3,4-octadecanetriol 
• 117168-59-9 (2S,3S,4R)-2-azido-1,3,4-octadecanetriol 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 554-62-1 D-ribo-phytosphingosine 

Relevant articles and documents

Sphingosine and Phytosphingosine from D-Threose Synthesis of a 4-Keto-Ceramide

Reaction of 2,4-O-benzylidene-D-threose 3 with tetradecyl magnesium bromide furnished D-arabino- and L-xylo-octadecane-1,2,3,4-tetrols 5a,x.Regioselective oxidation of the 4-OH group gave 4-keto-D-erythro-derivative 6 which can be reduced with acetaldehyde in a SmI2-catalyzed Tishtshenko reaction to afford exclusively 5a.Regioselective 2-O-mesylation of 5a ( -> 7a) and then acid catalyzed debenzylation afforded exclusively 2-O-mesyl-tetrol 9a.Reaction with NaN3 and ensuing azide reduction furnished D-ribo-C18-phytosphingosine (2) in high overall yield.Treatment of 2-O-mesyl derivatives 7a,x with NaN3 and then with 4-nitrobenzenesulfonyl chloride in pyridine afforded 11r,l.Elimination with DBU or, alternatively, by treatment with phenylselenide and then with H2O2, gave known 1,3-O-benzylidene protected azidosphingosine 14, which can be readily converted into sphingosine (1).Transformation of 2 into ceramide 15, selective 1,3-O-silyl protection, oxidation of the 4-OH group ( -> 17) and then desilylation afforded the 4-keto ceramide 18 found in a marine sponge.Reduction of 17 offers a convenient possibility for radioactive labelling of ceramides with tritium.