164385-87-9

Upstream product

• 115563-43-4 (2S,3S,4R)-2,3,5-tribenzyloxy-4-hydroxypentanal 
• 164988-64-1 (E)-(2R,3S,4R)-1,3,4-Tris-benzyloxy-icos-5-en-2-ol 
• 1944-80-5 pentadecyltriphenylphosphonium bromide 
• 20672-66-6 3,4,5-tri-O-benzyl-D-galactopyranose 
• 629-72-1 pentadecyl bromide 
• 124-63-0 methanesulfonyl chloride 
• 164385-86-8 (2R,3S,4R)-1,3,4-tri-O-benzyl-6-eicosane-1,2,3,4-tetrol 

Downstream Products

• 164988-76-5 (2S,3S,4R)-2-azido-1,3,4-tri-O-benzyl-1,3,4-eicosanetriol 
• 164989-10-0 C₈₁H₁₁₇NO₈ 
• 164988-88-9 Acetic acid (R)-1-((1S,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-nonadecylcarbamoyl)-pentacosyl ester 
• 164989-02-0 Acetic acid (R)-1-((1S,2S,3R)-2,3-dihydroxy-1-trityloxymethyl-nonadecylcarbamoyl)-pentacosyl ester 
• 164989-17-7 C₆₂H₁₀₃NO₈ 
• 164385-89-1 (1S,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-nonadecylamine 

Relevant academic research and scientific papers

Structure-activity relationship of α-galactosylceramides against b16- bearing mice

Agelasphin-9b, (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-16-methyl-2-[N- ((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(α- D-galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

Synthesis of Sphingosines, 11 - Convenient Synthesis of Phytosphingosine and Sphinganine from D-Galactal and D-Arabitol

3,4,6-Tri-O-benzyl-D-galactal (3) was directly converted into 3,4,6-tri-O-benzyl-2-deoxy-D-galactose (5).Wittig reaction of 5 with alkyltriphenylphosphonium salts in the presence of n-butyllithium as the base afforded olefins 6a, b which could be readily transformed into phytosphingosines 1a, b via different routes; (i) at first group introduction and then double bond and protective group removal, and azido group generation via hydrogenation; (ii) 2-O-mesylation, then double bond and benzyl group removal via hydrogenation, and finally nitrogen introduction; (iii) selective double bond hydrogenation, then nitrogen introduction, and finally benzyl group removal and amino group generation via hydrogenation.Wittig reaction of 5 with alkyltriphenylphosphonium salt in the presence of potassium tert-butoxide as the base afforded diene 7a which proved to be a convenient precursor for sphinganine syntheses; thus, 2-O-mesylation, then double bond and benzyl group removal via hydrogenation and 1,3-O-acetylation, and finally nitrogen introduction and de-O-acetylation afforded 23a.Based on the convenient transformation of D-arabitol into the 1,3-O-benzylidene derivative 25 a further phytosphingosine synthesis is outlined. - Key Words: Phytosphingosine / Sphinganine / Galactal / 2-Deoxy-D-galactose / D-Arabitol / Carbohydrates