128387-05-3

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 
• 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 
• 124-25-4 myristylaldehyde 
• 86120-41-4 methyl octadeca-2(E),4(E)-dien-1-oate 
• 93255-83-5 (2E,4E)-octadeca-2,4-dien-1-ol 
• 104808-42-6 1-trichloroacetimido-(2E,4E)-octadecadiene 
• 104808-77-7 trans-5-iodo-4-tetradec-(1E)-en-1-yl-2-trichloromethyl-4,5-dihydro-1,3-oxazine 
• 6036-85-7 (2R,3R,4E)-2-amino-octadec-4-ene-1,3-diol 

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 

Relevant academic research and scientific papers

Stereoselective synthesis of trans-olefins by the copper-mediated SN2′ reaction of vinyl oxazines with Grignard reagents. Asymmetric synthesis of d-threo-sphingosines

The SN2′ reaction of 6-vinyl-5,6-dihydro-4H-[1,3]oxazines with Grignard reagents in the presence of CuCN was studied, and high trans selectivity for the formation of double bond was observed with a variety of RMgX. The SN2′ reaction,

Stereoselective synthesis of β-amino alcohols: Practical preparation of all four stereomers of N-PMB-protected sphingosine from L- and D-serine

Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected α'-amino enone derivative 6, which was reduced with Zn(BH4)2 to the corresponding anti-β-amino alcohol in >96% de. On the other hand, N- PMB-N-Boc-protected α'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%.

Enantiopure aminotriol from D-isoascorbic acid synthesis of D-threo-C-18-sphingosine

Enantiopure suitably N,O-protected aminotriol has been prepared from D-isoascorbic acid. The utility of this homochiral building block in the synthesis of (2R,3R)-D-threo-C18-sphingosine is described via a Wittig reaction on a N,O-protected β-a

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.