157609-18-2

Upstream product

• 112-16-3 n-dodecanoyl chloride 
• 157609-17-1 3-O-benzyl-4,6-O-benzylidene-5a-carba-2-O-dodecanoyl-N-octadecyl-β-D-mannopyranosylamine 
• 124-30-1 1-aminooctadecane 
• 157609-15-9 3-O-benzyl-4,6-O-benzylidene-5a-carba-N-octadecyl-β-D-glucopyranosylamine 
• 157609-16-0 N-(3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-glucopyranosyl)-N-(octadecyl)dodecanamide 
• 142864-32-2 (1S,2R,3R,5R,8R,10S)-2-benzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0^3.8>undecane 

Relevant academic research and scientific papers

Pseudosugars, 33. Synthesis of Some 5a-Carbaglycosylamides, Glycolipid Analogs of Biological Interests

Five carbocyclic analogs of glycosylamides, N-(5a-carba-D-glycopyranosyl)-N-octadecyldodecanamides 2-6, having β-galacto, α- and β-gluco-, and α- and β-manno configurations, were synthesized by coupling of the protected anhydro derivatives 12, 15, and 21 of 5a-carba-sugars with octadecylamine, followed by N-acylation.Walden inversion of the 2-OH functions of 17 and 24 was carried out through O-sulfonylation.A bioassay (in vivo) of 5a-carbaglycosylamides showed that they are potent immunomodulators, obviously comparable to the true sugar analogs, suggesting that the 5a-carbasugar analogs may provide appropriate model compounds for biochemical studies in glycolipid chemistry. - Key Words: Carbohydrates / Pseudosugars / Cyclitols / Glycolipid analogs / Lipids, cyclitol / Glycosylamides, 5a-carba-