547763-55-3

Upstream product

• 604-69-3 β-D-glucose pentaacetate 
• 692740-54-8 phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 225241-34-9 phenyl 4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 791790-13-1 3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucal 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 547763-60-0 3*,6*-di-O-benzyl-L-glucal 
• 652972-16-2 3,4,6-tri-O-benzyl-L-galactal 
• 652972-17-3 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-L-galactopyranoside 
• 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 
• 652972-20-8 methyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-L-glucopyranoside 
• 652972-19-5 methyl 2-[acetyl(phenylsulfonyl)amino]-4-O-(2-acetyl-3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-L-glucopyranoside 
• 692740-51-5 3,6-di-O-benzyl-L-galactal 
• 692740-47-9 methyl 2-acetamido-4-O-(2-acetyl-3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-L-glucopyranoside 
• 692740-44-6 methyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-2-deoxy-2-phenylsulfonamido-β-L-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 
• 692740-46-8 Acetic acid (2R,3S,4R,5R,6S)-2-{(2S,3R,4S,5S,6S)-5-(acetyl-benzenesulfonyl-amino)-4-benzyloxy-2-benzyloxymethyl-6-[2-(4-methoxy-benzyloxy)-ethoxy]-tetrahydro-pyran-3-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 692740-49-1 methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside 

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.

Conversion of D-Glucals into L-Glycals and Mirror-Image Carbohydrates

(Equation presented) L-Glycals can be prepared in seven steps from readily available D-glucals, enabling the facile construction of mirror-image carbohydrates such as the L-lactosamine derivative shown above.