102822-90-2

Upstream product

• 55941-97-4 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 
• 112-67-4 n-hexadecanoyl chloride 
• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 
• 65751-67-9 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 
• 76679-67-9 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1,2-di-O-(but-2-enyl)-sn-glycerol 
• 4196-36-5 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 76679-67-9 (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-{2,3-bis-[((E)-but-2-enyl)oxy]-propoxy}-tetrahydro-pyran 

Downstream Products

• 28069-25-2 1,2-di-O-palmitoyl-3-O-α-D-glucopyranosyl-sn-glycerol 

Relevant academic research and scientific papers

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.

Synthesis of phosphatidyl-α-glucosyl-diacylglycerol containing palmitic and oleic acid esters

The recently introduced 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane protecting group enabled us to synthesize a naturally occurring phosphatidyl-α-glucosyl-diacylglycerol via a phosphotriester intermediate.