65751-67-9

Upstream product

• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 
• 76679-67-9 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1,2-di-O-(but-2-enyl)-sn-glycerol 
• 30760-09-9 methyl 1-deoxy-1-thio-β-D-glucopyranoside 
• 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 
• 13350-45-3 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 104992-64-5 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 83-87-4 D-glucose pentaacetate 
• 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

• 55941-98-5 Hexadecanoic acid 1-hexadecanoyloxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 
• 108811-06-9 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 
• 102822-90-2 3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1,2-di-O-palmitoyl-sn-glycerol 
• 28069-25-2 1,2-di-O-palmitoyl-3-O-α-D-glucopyranosyl-sn-glycerol 
• 108811-04-7 1,2-anhydro-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 
• 108811-05-8 2,3-anhydro-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 
• 108811-09-2 1-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-deoxy-2(R)-glycerol 
• 108811-10-5 1-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-deoxy-2(S)-glycerol 
• 108811-08-1 1-O-benzoyl-2-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 
• 108811-07-0 1-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 

Relevant academic research and scientific papers

Quantitation in the regioselectivity of acylation of glycosyl diglycerides: total synthesis of a Streptococcus pneumoniae α-glucosyl diglyceride

The fidelity of acylation regioselectivity in the synthesis of mixed glycosyl diacylglycerols can be accurately measured by quantitative 13C NMR spectroscopy using a 1-13C-labelled fatty acid and a paramagnetic relaxation enhancement agent. Exquisite regioselectivity is achieved using a stepwise acylation/substitution of a glycosyl β-bromohydrin, which is applied to the total synthesis of Streptococcus pneumoniae Glc-DAG-s2.

Synthetic Studies on Rhynchosporoside and Related Substances

The stereoselective synthesis of the 1-O-α-D-glucopyranosides and 1-O-α-D-cellobiosides of 3-deoxy-2(R)- and 2(S)-glycerols to determine the complete stereochemistry of rhynchosporoside, which is a host selective phytotoxin from Rhynchosporium secalis, is

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.