143615-69-4

Upstream product

• 94676-99-0 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 
• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 94676-99-0 N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 
• 114697-01-7 (+/-)-N-(4c-pentadec-1-ynyl-2r-phenyl-[1,3]dioxan-5c-yl)-acetamide 
• 114697-01-7 (+/-)-N-(4t-pentadec-1-ynyl-2r-phenyl-[1,3]dioxan-5t-yl)-acetamide 
• 78779-96-1 N,O,O-triacetyl-L-threo-C₁₈-sphingosine 
• 108-24-7 acetic anhydride 
• 25695-95-8 (2S,3S,4E)-L-threo sphingosine 
• 75-36-5 acetyl chloride 
• 890027-23-3 (2S,3S,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride 
• 143517-04-8 N-[(1S,2R)-3-[(4-Methoxy-phenyl)-diphenyl-methoxy]-2-(2-trimethylsilanyl-ethoxymethoxy)-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-acetamide 
• 143517-05-9 N-[(1S,2R)-3-Oxo-2-(2-trimethylsilanyl-ethoxymethoxy)-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-acetamide 
• 128308-04-3 N-[(1S,2R)-3-Hydroxy-2-(2-trimethylsilanyl-ethoxymethoxy)-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-propyl]-acetamide 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 

Downstream Products

• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 2482-37-3 (+/-)-threo-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 35301-24-7 C2-dihydroceramide 
• 78779-96-1 N,O,O-triacetyl-L-threo-C₁₈-sphingosine 

Relevant academic research and scientific papers

Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase

Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.

Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells

Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4+ T cells, is an important stimulus for the switch of th

The synthesis and biological characterization of a ceramide library

A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright

Efficient enantioselective syntheses of chloramphenicol and (D)-threo- and (D)-erythro-sphingosine

The chiral diazaborolidine 1 has been applied to the enantioselective syntheses of chloramphenicol (2) and (D)-threo-N-acetylsphingosine (3), a synthetic precursor of the diastereomeric (D)-sphingosines. (C) 2000 Elsevier Science Ltd.

Improved, gram scale synthesis of N,O,O-triacetyl-erythro- and threo-C18-sphingosines from serine

A formal total synthesis of all four (E)C18-sphingosine stereoisomers from serine has been carried out. This involves the thiazole-based homologation of the amino acid into a chiral 3-amino-2,4-dihydroxybutanal 1 and the Wittig olefination of 1 with the ylide from the C14 alkyl phosphonium salt 2. The photoisomerization of the resulting mixture of Z- and E-alkenes affords the target sphingosine. Thus, N,O,O-triacetyl-D-erythro C18-sphingosine 5 and the L-threo isomer 10 were prepared in 43-44% overall yield from the aldehyde (S,S)-1a and (2R,3S)-1b, respectively. The corresponding antipodal L-erythro and D-threo isomers can be prepared in the same way starting from aldehydes ent-1a and ent-1b, respectively. Conversion of the above acetyl sphingosines into the free sphingoid bases has been reported in the literature.

Diastereo- and Enantioselective Synthesis of L-threo- and D-erythro-Sphingosine

L-threo-sphingosine and its D-erythro isomer (1) are subunits of many glycosphingolipids, gangliosides and ceramides.This paper describes the highly diastereo- and enantioselective synthesis of both isomers (de,ee>98percent).The key steps in the synthesis are the aldol reaction of the SAMP hydrazone (S)-2 with racemic α-phenylselenylpentadecanal 3, the diastereoselective triacetoxyborohydride reduction of ketone 5 and exclusive (E) C=C double bond formation in the elimination of hydroxyl and selenyl moieties promoted by methanesulfonyl chloride.Mesylate 8 was then readily converted via the 1,3-O-acetonide-protected azidosphingosine 9 to L-threo-sphingosine.Conversion to the known 1-O,2-N-diacetyl-protected sphingosine 13 with subsequent Mitsunobu inversion of the C3-OH centre afforded the D-erythro-sphingosine epimer. - Keywords: asymmetric syntheses . alkenylations .SAMP/RAMP hydrazones . selenyl aldehydes . sphingosine

Syntheses of two pairs of enantiomeric C18-sphingosines and a palmitoyl analogue of gaucher spleen glucocerebroside

Sixteen kinds of chiral C4-epoxides [(-)-10a-d,(+)-10a-d,(-)-11a-d,(+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1,4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a,(-)-10a,(-)-11a,(+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.

Synthesis of two pairs of enantiomeric C18-sphingosines

Two pairs of enantiomeric (D-erythro, L-erythro, D-threo, L-threo) C18-sphingosines have been synthesized from Z-butene-1,4-diol utilizing Sharpless asymmetric epoxidation and a regiospecific ring-opening reaction of the resulting C4-chiral epoxide with an azide anion.

A novel, efficient synthesis of (±)-erythro-sphingosine

A stereoselective synthesis of (±)-erythro-sphingosine triacetate (1) is described. The key reaction that determines the right stereochemistry is the iodocyclization of 1-trichloroacetimido-(2E,4E)-octadecadiene (5). The 4,5-dihydro-1,3-oxazine (6) through cleavage with HCl and treatment with Amberlyst A 26 in the AcO- form, followed by full acetylation, affords (1) in good yield.