164576-08-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 80924-06-7 1,3-O-benzylidene D-arabitol 
• 100-52-7 benzaldehyde 
• 488-82-4 D-Arabitol 

Downstream Products

• 745042-02-8 (2S,3S,4R)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-(tetracosanoylamino)nonane-3,4-diol 
• 745041-79-6 (2S,3S,4R)-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-tetracosanoylamino-1,3,4-nonanetriol 
• 745041-64-9 (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol 
• 745041-72-9 (2S,3S,4R)-2-amino-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol 
• 745041-30-9 (2R,3S,4R)-1,3-O-benzylidene-2-O-methanesulfonyl-1,2,3,4-nonanetetrol 
• 745041-21-8 (2R,3S,4R)-1,3-O-benzylidene-1,2,3,4-nonanetetrol 
• 383187-82-4 OCH 
• 164576-09-4 4,5-anhydro-1,3-O-benzylidene-D-arabinitol 

Relevant academic research and scientific papers

Total synthesis of an immunosuppressive glycolipid, (2S,3S,4R)-1-O- (α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol

(Chemical Equation Presented) A practical and efficient total synthesis of (2S,3S,4R)-1-O-(α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol, OCH 1b, a potential therapeutic candidate for Th1-mediated autoimmune diseases, is described. The synthesis

GLYCOLIPID DERIVATIVES, PROCESS FOR PRODUCTION OF THE SAME, INTERMEDIATES FOR SYNTHESIS THEREOF, AND PROCESS FOR PRODUCTION OF THE INTERMEDIATES

Novel glycolipid derivatives, where the substituent of the sphingosine base part is a short carbon chain alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group and

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