692740-46-8

Upstream product

• 13807-89-1 2-(4-methoxybenzyloxy)ethanol 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 225241-34-9 phenyl 4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 692740-45-7 ethyl 4-O-(2-acetyl-3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phenylsulfonamido-1-thio-β-L-glucopyranoside 
• 692740-54-8 phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 692740-51-5 3,6-di-O-benzyl-L-galactal 
• 604-69-3 β-D-glucose pentaacetate 
• 652972-18-4 Acetic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-((2S,3R,4S)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 652972-17-3 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-L-galactopyranoside 
• 547763-55-3 (2S,3S,4S,5R,6R)-4-Benzyloxy-2-benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol 
• 652972-16-2 3,4,6-tri-O-benzyl-L-galactal 
• 791790-13-1 3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucal 
• 547763-60-0 3*,6*-di-O-benzyl-L-glucal 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Relevant academic research and scientific papers

Mirror-Image Carbohydrates: Synthesis of the Unnatural Enantiomer of a Blood Group Trisaccharide

Methyl D-glucoside and D-glucose pentaacetate are transformed, respectively, into methyl α-O-glucuronide 3 and hydroxymethyl β-C-glucuronide 9, which undergo decarboxylative elimination efficiently to produce 4-deoxypentenoside 4 and L-glucal 10. These unsaturated pyranosides provide an expeditious entry into mirror-image oligosaccharides, as demonstrated in the synthesis of the unnatural enantiomer of the H-type II blood group determinant trisaccharide (D-Fuc-(α1-2)-L-Gal-(β 1-4)-L-GlcNAc-β-OMe). This work illustrates that D-glucose, a common starting material in the synthesis of naturally occurring carbohydrates, can also be used to prepare their mirror-image analogues.