80738-62-1

Upstream product

• 100-39-0 benzyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 38081-38-8 3,4,6-tri-O-acetyl-1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose 
• 55659-53-5 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-d-glucopyranose 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 65827-59-0 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 
• 80738-51-8 Acetic acid (2R,3R,4S,5S,6S)-2-acetoxymethyl-3,5-bis-benzyloxy-6-((2R,3S,4S,5S,6S)-3,5-bis-benzyloxy-4-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester 
• 80738-52-9 methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 65827-55-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 55659-53-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 

Downstream Products

• 158818-92-9 3,4,6-tri-O-benzyl-α-D-arabino-hexopyranose-2-ulosyl bromide 
• 40246-34-2 (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one 
• 112330-11-7 (3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside 
• 138181-77-8 iso-propyl 3,4,6-tri-O-benzyl-β-D-mannopyranoside 
• 158818-95-2 ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-arabino-hexopyranosid-2-ulose 
• 158818-97-4 isopropyl 3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosid-2-ulose 
• 158818-96-3 phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-arabino-hexopyranosid-2-ulose 
• 158852-32-5 ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-mannopyranoside 
• 1017968-93-2 3,4,6-tri-O-benzyl-1,5-anhydro-D-fructose E-oxime 
• 1017968-98-7 3,4,6-tri-O-benzyl-1,5-anhydro-D-fructose 

Relevant academic research and scientific papers

D-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose, d-mannose, and 2-deoxy-d-glucose

Altered carbohydrate metabolism in cancer cells was first noted by Otto Warburg more than 80 years ago. Upregulation of genes controlling the glycolytic pathway under normoxia, known as the Warburg effect, clearly differentiates malignant from non-maligna

Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (-)-bissetone and (-)-palythazine

High-yielding protocols are described to convert d-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and β-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-d-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale.

An efficient one step dihydroxylation of 1,2-glycals with oxone in acetone

A number of glycals have been converted into the corresponding 1,2-diols in fair to good yields. The reaction appears to proceed via the corresponding epoxide which opens in situ.

3,4,6-Tri-O-benzyl-α-D-arabino-hexopyranos-2-ulosyl Bromide: A Versatile Glycosyl Donor for the Efficient Generation of β-D-Mannopyranosidic Linkages

An expedient four-step sequence is described for the conversion of acetobromoglucose into the title 2-oxohexosyl ("ulosyl") bromide 4.Due to its O-benzyl protection, 4 is considerably more reactive than its acylated analogs 1-3: Ag2CO3-promoted glycosidat

RECONSTRUCTION OF GLYCAN CHAINS OF GLYCOPROTEIN BRANCHING MANNOPENTAOSIDE AND MANNOHEXAOSIDE

Synthetic routes to the branching mannopentaoside 4 and mannohexaoside 5 are described employing properly protected mannobioside 13 as a key intermediate.