158227-70-4

Upstream product

• 39483-53-9 2,3,4-tri-O-benzyl-6-O-p-nitrobenzoyl-α-D-glucopyranosyl bromide 
• 88567-49-1 6-O-acetyl-2,3,4,-tri-O-benzyl-α-D-glucopyranose 
• 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 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 112-67-4 n-hexadecanoyl chloride 
• 14912-92-6 caesium palmitate 
• 176911-83-4 (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran 

Downstream Products

• 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 
• 158227-72-6 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-{(2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2-bromo-ethoxy)-hydroxy-phosphoryloxymethyl]-tetrahydro-pyran-2-yloxy}-ethyl ester 
• 28069-25-2 1,2-di-O-palmitoyl-3-O-α-D-glucopyranosyl-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 and absolute configuration of 6-O-phosphocholine-α-D-glucopyranosyl glycerolipid isolated from HTLV-I-infected cell lines

Syntheses of both stereoisomers of α-D-glucopyranosylglycerolipids enabled us to confirm the structure and the (2S)-configuration of a new glycoglycerolipid isolated from HTLV-I infected T-cell lines.