116447-99-5

Basic information

• Product Name: (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol
• Synonyms: (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol
• CAS NO: 116447-99-5
• Molecular Weight: 626.02
• Mol File: 116447-99-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol(116447-99-5)
• EPA Substance Registry System: (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol(116447-99-5)

Safety Data

• Hazardous Substances Data: 116447-99-5(Hazardous Substances Data)

Upstream product

• 1492-30-4 4-nitrophenyl palmitate 
• 117112-63-7 (2S,3R,4E)-2-amino-1,3-benzylidene-4-octadecene-1,3-diol 
• 112-67-4 n-hexadecanoyl chloride 
• 112-71-0 1-Bromotetradecane 
• 57-10-3 1-hexadecylcarboxylic acid 
• 99274-32-5 2,4-O-benzylidene-D-threose 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 3006-41-5 4,6-O-benzylidene-α,β-D-galactopyranose 
• 124313-98-0 (2R,3R,4E)-1,3-benzylidene-2-methanesulfonyl-4-octadecene-1,2,3-triol 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 117112-62-6 (2R,3R)-cis-1,3-O-benzylidene-1,2,3-octadec-4-enetriol 

Downstream Products

• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 117112-65-9 (2S,3R)-3-O-benzoyl-4,5-dihydro-1-deoxyceramide-1-bromide 
• 34324-89-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene 
• 117112-66-0 (2S,3R)-3-O-benzoyl-4,5-dihydro-1-deoxyceramide-1-sulfonic acid 
• 143517-08-2 1-OTBDPS ceramide 
• 143517-09-3 Benzoic acid (E)-(R)-1-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester 
• 94069-99-5 (2S,3R)-N-palmitoyl-3-O-benzoyl-1-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-sphingosine 
• 117112-64-8 (2S,3R)-N-palmitoyl-1,3-O-benzylidene-4,5-dihydro-D-sphingosine 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 

Relevant articles and documents

The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog

The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous ( > 99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.

SYNTHESIS OF D-ERYTHRO-1-DEOXYDIHYDROCERAMIDE-1-SULFONIC ACID

New D-erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable lipids in a non-photosynthetic marine diatom Nitzschia alba, was synthesized from galactose as a chiral precursor using the Hanessian-Hullar reaction as the key step in the