28069-25-2

Upstream product

• 102822-90-2 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1,2-di-O-palmitoyl-sn-glycerol 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 4196-36-5 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate 
• 65751-67-9 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 
• 14912-92-6 caesium palmitate 
• 158227-69-1 Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester 
• 158227-71-5 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 
• 158227-70-4 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[(2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester 
• 88567-49-1 6-O-acetyl-2,3,4,-tri-O-benzyl-α-D-glucopyranose 
• 76679-67-9 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1,2-di-O-(but-2-enyl)-sn-glycerol 

Relevant academic research and scientific papers

An easy α-glycosylation methodology for the synthesis and stereochemistry of mycoplasma α-glycolipid antigens

Mycoplasma fermentans possesses unique α-glycolipid antigens (GGPL-I and GGPL-III) at the cytoplasm membrane, which carry a phosphocholine group at the sugar primary (6-OH) position. This paper describes a practical synthetic pathway to a GGPL-I homologue (C16:0) and its diastereomer, in which our one-pot α-glycosylation method was effectively applied. The synthetic GGPL-I isomers were characterized with 1H NMR spectroscopy to determine the equilibrium among the three conformers (gg, gt, tg) at the acyclic glycerol moiety. The natural GGPL-I isomer was found to prefer gt (54%) and gg (39%) conformers around the lipid tail, while adopting all of the three conformers with equal probability around the sugar position. This property was very close to what we have observed with respect to the conformation of phosphatidylcholine (DPPC), suggesting that the Mycoplasma glycolipids GGPLs may constitute the cytoplasm fluid membrane together with ubiquitous phospholipids, without inducing stereochemical stress.

Synthesis of phosphatidyl-α-glucosyl glycerol containing a dioleoyl phosphatidyl moiety. Application of the tetraisopropyldisiloxane-1,3-diyl (tips) protecting group in sugar chemistry. part III1 1 For part I and II see references 11 and 39, respectively.

In this study we demonstrate that the tetraisopropyldisiloxane-1,3-diyl protecting group could be introduced, in a two step procedure, at the 3'- and 4'-hydroxyl functions of α-glucosyldiglyceride 3 to give derivative 6. Compound 6 could be selectively condensed with a suitably protected phosphatidyl part 9 at its primary hydroxyl function to afford the protected glycophospholipid 10a. The phosphatidyl part 9 was obtained by phosphorylation of optically pure 1,2-di-O-oleoyl-sn-glycerol (8a) with phosphoditriazolide 7b. Finally, the 2,4-dichlorophenyl and TIPS protecting groups were removed from 10a by syn-4-nitro-benzaldoximate and fluoride ions, respectively, to afford glycophospholipid 10c.