128387-01-9

Upstream product

• 3102-57-6 N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadec-3c-enyl)-acetamide 
• 108-24-7 acetic anhydride 
• 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 
• 123-78-4 dl-threo-sphingosine 
• 3102-57-6 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadec-3c-enyl)-acetamide 
• 123-78-4 D,L-Sphingosin 
• 94676-99-0 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 
• 123-78-4 erythro-(E)-2-amino-4-octadecene-1,3-diol 
• 104847-90-7 trans-2-hydroxymethyl-3-pentadec-(1E)en-1-yl-aziridine 
• 124-25-4 myristylaldehyde 
• 104808-77-7 trans-5-iodo-4-tetradec-(1E)-en-1-yl-2-trichloromethyl-4,5-dihydro-1,3-oxazine 
• 195194-58-2 (2S,3R)-2-N-acetylamino-1,3-dihydroxyoctadec-4-ene 

Downstream Products

• 3102-57-6 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadec-3c-enyl)-acetamide 
• 81819-46-7 N-[(2R,4S,5R)-4-((E)-Pentadec-1-enyl)-2-phenyl-[1,3]dioxan-5-yl]-acetamide 
• 2482-37-3 (2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene 

Relevant academic research and scientific papers

An efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenine and related compounds from 2-amino-2-deoxy-D-glucose.

Efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenines having C16, C18, and C20 carbon-chains was achieved in 13 steps, starting from allyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. 2-Amino-1,6-di-O-tert- butyldiphenylsilyl-2-N,3-O-carbonyl-2-deoxy-D -allitol was used as the key intermediate.

Asymmetric synthesis of vicinal amino alcohols: Xestoaminol C, sphinganine and sphingosine

The highly diastereoselective anti-aminohydroxylation of α,β-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps). The Royal Society of Chemistry 2008.

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.

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.