138181-77-8

Upstream product

• 38081-38-8 3,4,6-tri-O-acetyl-1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 158818-92-9 3,4,6-tri-O-benzyl-α-D-arabino-hexopyranose-2-ulosyl bromide 
• 80738-62-1 2-O-acetyl-3,4,6-tri-O-benzyl-1,5-anhydro-D-arabino-hex-1-enitol 
• 55659-53-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 138181-75-6 ((3S,4S,5R,6R)-2-Benzenesulfinyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-isopropoxy-dimethyl-silane 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 

Relevant academic research and scientific papers

Experimental evidence on the hydroxymethyl group conformation in alkyl β-D-mannopyranosides

A rotational population study of the hydroxymethyl group of alkyl β-D-mannopyranosides was performed by means of CD and NMR spectroscopy. Three different benzyl, acetyl, and p-bromobenzoyl series of alkyl β-D-mannopyranosides with different chiral and non

Manno- versus gluco-Selectivity in reductions of 2-keto-β-D-arabino-hexopyranosides

Tri-sec-butylborohydrides (L- or K-Selectride) reduce the carbonyl group in acylated 2-keto-β-D-arabino-hexopyranosides to β-D-mannosides in an essentially stereospecific fashion, whereas borane reduction gives the 2-epimeric β-D-glucosides with high preference. As preparative yields are in the 70-85% range, the ulosyl donor approach can thus be utilized for the straightforward construction of oligosaccharides containing either β-D-Man or β-D-Glc units.

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