124313-98-0

Upstream product

• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 124-63-0 methanesulfonyl chloride 
• 112-71-0 1-Bromotetradecane 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 3006-41-5 4,6-O-benzylidene-α,β-D-galactopyranose 
• 99274-32-5 2,4-O-benzylidene-D-threose 
• 117112-62-6 (2R,3R)-cis-1,3-O-benzylidene-1,2,3-octadec-4-enetriol 
• 100-52-7 benzaldehyde 

Downstream Products

• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 117112-64-8 (2S,3R)-N-palmitoyl-1,3-O-benzylidene-4,5-dihydro-D-sphingosine 
• 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 
• 124338-03-0 Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester 
• 94069-99-5 Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 108283-59-6 (2S,3R,4E)-2',3',4',6'-tetraacetyl-β-D-glucopyranosyl-(1'<->1)-2-azido-3-benzoyl-4-octadecene-1,3-diol 
• 108283-58-5 (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 74365-77-8 glucosylceramide 

Relevant academic research and scientific papers

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.

SYNTHESES OF D-ERYTHRO-1-DEOXYDIHYDROCERAMIDE-1-SULFONIC ACID AND PHOSPHONOSPHINGOGLYCOLIPID FOUND IN MARINE ORGANISM VIA A COMMON PRECURSOR

D-Erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable hydrogenated lipids in a non-photosynthetic marine diatom, Nitzschia alba, and (2S,3R)-N-palmitoyl-1-O--β-D-galactopyranosyl>-D-sphingosine, found in marine snail Turbo cornutus were synthesized via a common precursor (10) starting from galactose.

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