117168-55-5

Basic information

• Product Name: (2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol
• Synonyms: (2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol
• CAS NO: 117168-55-5
• Molecular Weight: 406.606
• Mol File: 117168-55-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol(117168-55-5)
• EPA Substance Registry System: (2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol(117168-55-5)

Safety Data

• Hazardous Substances Data: 117168-55-5(Hazardous Substances Data)

Upstream product

• 112-71-0 1-Bromotetradecane 
• 909277-52-7 2,4-O-benzylidene-D-tetraose 
• 150162-78-0 (2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one 
• 88303-25-7 tetradecylmagnesium bromide 
• 99274-32-5 2,4-O-benzylidene-D-threose 
• 303752-90-1 1,3-O-benzylidene-(D-arabino/L-xylo)-1,2,3,4-octadecanetetrol 

Downstream Products

• 1068608-25-2 2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol 
• 1431220-32-4 C₆₅H₉₅NO₈S 
• 1431220-33-5 C₆₆H₉₇NO₈S 
• 1431220-34-6 C₆₂H₉₁NO₈S 
• 1431220-35-7 C₆₃H₉₃NO₈S 
• 1431220-28-8 C₄₁H₇₃NO₈S 
• 1431220-29-9 C₄₂H₇₅NO₈S 
• 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 
• 117168-58-8 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 
• 117168-66-8 (2S,4R,5R)-4-[(R)-1-hydroxypentadecyl]-2-phenyl-1,3-dioxan-5-yl methanesulfonate 

Relevant articles and documents

Synthesis and immunostimulatory activity of two α-S-galactosyl phenyl-capped ceramides

Two α-S-linked galactosylceramides carrying ω-phenyl fatty acid chains were efficiently synthesized and were shown to have in vitro stimulatory activity for human natural killer T cells. ARKAT-USA, Inc.

SYNTHESIS OF D-ribo- AND L-lyxo-PHYTOSPHINGOSINE: TRANSFORMATION INTO THE CORRESPONDING LACTOSYL-CERAMIDES

2,4-O-Benzylidene-D-threose (2) reacted with tetradecylmagnesium bromide to give the D-arabino- and the L-xylo-octadecanetetrol derivatives 3a and 3x as a readily separable mixture.Each of these compounds was transformed, via regioselective mesylation, azide displacement, benzylidene cleavage, and azide reduction, into D-ribo- (1r) and L-lyxo-phytosphingosine (1l), respectively. 3,4-O-Isopropylidenation of the intermediate azido derivatives 7r and 7l afforded the 1-O-glycosyl acceptors 2-azido-3,4-O-isopropylidene-D-ribo-1,3,4-octadecanetriol (8r) and 2-azido-3,4-O-isopropylidene-L-lyxo-1,3,4-octadecanetriol (8l), respectively.With the trichloroacetimidate-activated lactosyl donor 9, the expected glycosydes 2-azido-1-O-(2,3,6,2',3',4'6'-hepta-O-acetyl-β-lactosyl)-3,4-O-isopropylidene-D-ribo- and L-lyxo-1,3,4-octadecanetriol (10r and 10l) were obtained, which were conveniently transformed into the corresponding unprotected glycosphingolipids 14r and 14l.