4201-55-2

Basic information

• Product Name: Hexadecanamide, N-[(1S,2R,3E)-2-(benzoyloxy)-1-(hydroxymethyl)-3-heptadecenyl]-
• CAS NO: 4201-55-2
• Molecular Formula: C41H71NO4
• Molecular Weight: 642.019
• Mol File: 4201-55-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Hexadecanamide, N-[(1S,2R,3E)-2-(benzoyloxy)-1-(hydroxymethyl)-3-heptadecenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexadecanamide, N-[(1S,2R,3E)-2-(benzoyloxy)-1-(hydroxymethyl)-3-heptadecenyl]-(4201-55-2)
• EPA Substance Registry System: Hexadecanamide, N-[(1S,2R,3E)-2-(benzoyloxy)-1-(hydroxymethyl)-3-heptadecenyl]-(4201-55-2)

Safety Data

• Hazardous Substances Data: 4201-55-2(Hazardous Substances Data)

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 94069-97-3 Hexadecanoic acid ((E)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadec-3-enyl)-amide 
• 98-88-4 benzoyl chloride 
• 94069-98-4 Benzoic acid (E)-(R)-1-((S)-1-hexadecanoylamino-2-trityloxy-ethyl)-hexadec-2-enyl ester 
• 102874-34-0 [(4S,5R)-5-((E)-Pentadec-1-enyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-methanol 
• 144150-66-3 2-phenyl-(2,3-dideoxy-4,6-O-ethylidene-D-allopyranoso)<2,3-d>-4,5 dihydrooxazole 
• 144150-67-4 (2R,4R,5R)-4-((4S,5S)-4-Hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-2-methyl-[1,3]dioxan-5-ol 
• 144150-68-5 (3aS,6aS)-2-Phenyl-3a,4,6,6a-tetrahydro-furo[3,4-d]oxazol-6-ol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 6847-14-9 N-benzoyl-D-glucosamine 
• 911-74-0 3-O-benzoylsphingosine hydrochloride 
• 112-67-4 n-hexadecanoyl chloride 
• 202464-96-8 (2R,3R,4E)-3-benzoyloxyoctadec-4-ene-1,2-diol 
• 202464-95-7 (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol 

Downstream Products

• 74365-77-8 glucosylceramide 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 536-14-1 N-palmitoyl-D-erythro-sphingomyelin 
• 34324-89-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene 
• 167871-75-2 (2S,3R,4E)-[2',3',6'-tri-O-benzoyl-4'-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol 
• 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 
• 94069-99-5 Benzoic acid (E)-(R)-1-[(S)-1-hexadecanoylamino-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 94069-99-5 Benzoic acid (E)-(S)-1-[(R)-1-hexadecanoylamino-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 4201-58-5 D-erythro-N-Palmitioyl-sphingonin 

Relevant articles and documents

NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.

METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS

The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.

The total synthesis of ganglioside GM3

Previous syntheses of ganglioside GM3 (NeuAcα3Galβ4Glcβ1Cer) are reviewed, and both chemoenzymatic and chemical total synthetic approaches were investigated. In a chemoenzymatic approach, (2S,3R,4E)-5'''-acetyl-α-neuraminyl-(2''' → 3'')-β-galactopyranosyl-(1'' → 4')-β-glucopyranosyl-(1' mutually implies 1)-2-azido-4-octadecene-1,3-diol (azidoGM3) was readily prepared utilizing recombinant β-Gal-(1'' → 3'/4')-GlcNAc α-(2''' → 3'')-sialyltransferase enzyme, and was evaluated as a synthetic intermediate to ganglioside GM3. The chemical total synthesis of ganglioside GM3 was performed on one of the largest scales yet reported. The highlights of this synthesis include minimizing the steps necessary to prepare the lactosyl acceptor as a useful anomeric mixture, which was present in excess for the highly regioselective and fairly stereoselective sialylation with a known neuraminyl donor to give the protected GM3 trisaccharide. The synthetic methodology maximized convergence by a subsequent glycosidic coupling of the well-characterized GM3 trisaccharide trichloroacetimidate derivative with protected ceramide. The ganglioside GM3 was nearly homogeneous as the two glycosidic couplings utilized preparative HLPC purifications, and variations in the sphingosine base and fatty acyl group were under 0.1 and 0.2%, respectively. (C) 2000 Elsevier Science Ltd.