118073-41-9

Upstream product

• 117363-50-5 (6S)-<6-2H>Methyl-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 698348-45-7 methyl 2,3,4-tri-O-benzyl-β-D-(6,6-2H2)glucopyranoside 
• 23403-55-6 D-<6,6-(2)H2>glucose 
• 86448-07-9 6-(S)-6-(2)H1-1,6-anhydro-β-D-glucopyranose 

Downstream Products

• 131904-51-3 (6S)-<6-2H>Methyl 2,3,4-tri-O-benzyl--(2-6)-β-D-glucopyranoside 
• 131904-51-3 (6S)-<6-2H>Methyl 2,3,4-tri-O-benzyl--(2-6)-β-D-glucopyranoside 
• 131904-53-5 (6S)-<6-2H>Methyl 2,3,4-tri-O-benzyl--(2-6)-β-D-glucopyranoside 
• 131904-53-5 (6S)-<6-2H>Methyl 2,3,4-tri-O-benzyl--(2-6)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Stereoselective synthesis of chirally deuterated (S)-D-(6- 2H1)glucose

Chirally deuterated (S)-D-(6-2H1)glucose has been prepared in good overall yield from D-(6,6′-2H 2)glucose by a short, five-step synthesis from D-(6,6- 2H2)glucose utilizing (R)-(+)-Alpine-Borane [(R)-9-[(6,6-dimethylbicyclo[3.1.1]hept-2-yl)methyl]-9- borabicyclo[3.3.1]nonane]. Suitably protected methyl 2,3,4-tri-O-benzyl-D-(6,6- 2H2)glucopyranoside was prepared and the deuterated O-6 primary alcohol was oxidized to an aldehyde by Swern oxidation. Stereoselective reduction with nondeuterated (R)-(+)-Alpine-Borane gave methyl 2,3,4-tri-O-benzyl-(6S)-D-(6-2H1)glucopyranoside, which was deprotected under standard conditions to afford the title compound. The key stereoselective reduction step was achieved in 90% yield. The preparation uses economical, commercially available starting materials and will be useful for elucidating biosynthetic mechanisms.

The function of the 5-hydroxymethyl group of lactose in enzymatic hydrolysis with beta-galactosidase from E. coli.

A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-2H]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidas

Preferred Conformation about the C5-C6 Bond of N-Acetylneuraminyl(2-6)-D-galacto- and D-glucopyranosides in Solution

Diastereoselective deuteration and 1H NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-β-D-hexopyranosides .In aqueous solution, NeuNAcα(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = 60:40:0), and NeuNAcβ(2-6)Gal exists equally in the three conformers.

Synthesis of 6-(S) Deuterium-Labelled Derivatives of Maltose and Isomaltose

The 6-(S) deuterium-labelled compounds methyl β-isomaltoside (4a), methyl β-maltoside (8a) and methyl 4,6-di-O-(α-D-glucopyranosyl)-β-D-glucopyranoside (12) have been synthesized from deuterium-substituted 1,6-anhydro compounds.The 6-(R) deuterium-labelled compound methyl β-maltoside (10) has been prepared by inversion at the 6-position of the corresponding 6-(S) derivative.The compounds have all been examined by (1)H NMR spectroscopy at 500 MHz and their preferred solution conformation has been inferred from the J56R and J56S coupling constants.