69973-32-6

Usage

Uses

Methyl β-Xylobioside is a disaccharide used extensively in carbohydrate research.

InChI:InChI=1/C11H20O9/c1-17-10-9(16)7(14)5(3-19-10)20-11-8(15)6(13)4(12)2-18-11/h4-16H,2-3H2,1H3/t4-,5-,6+,7+,8-,9-,10-,11+/m1/s1

Upstream product

• 68977-81-1 methyl-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside 
• 78423-96-8 methyl-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside 
• 78437-56-6 methyl O-(2,3-di-O-acetyl-4-O-benzyl-β-D-xylopyranosyl)-(1-> 4)-2,3-di-O-acetyl-β-D-xylopyranoside 
• 70003-50-8 methyl 2,3-di-O-acetyl-β-D-xylopyranoside 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 121947-41-9 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3R,4S,5R)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 887257-01-4 2,3,2',3',4'-penta-O-acetyl-α-D-xylobiosyl trichloroacetimidate 

Relevant academic research and scientific papers

Synthesis of regioselectively sulfated xylodextrins and crystal structure of sodium methyl β-d-xylopyranoside 4-O-sulfate hemihydrate

Methyl xylobioside and methyl xylotrioside were prepared from the peracetylated anomeric xylosyl trichloroacetimidates by reaction with methanol followed by Zemplen deacetylation. Methyl β-d-xylopyranoside, methyl β-d-xylobioside and methyl β-d-xylotrioside were subjected to treatment with dibutyltin oxide followed by reaction with the trimethylamine/sulfur trioxide complex in tetrahydrofuran. This way, preferential sulfation of the terminal 4-hydroxy group at the nonreducing xylopyranosyl unit was achieved. In addition, partial sulfation at position 2 of the distal xylose unit was observed. The substitution pattern was derived from NMR spectroscopic data and was confirmed by the X-ray structure determination of sodium methyl β-d-xylopyranoside 4-O-sulfate. The compound crystallized as a hemihydrate in a triclinic lattice of space group P1 and possesses a pseudomonoclinic 2D supramolecular structure. The sulfation of free pentose oligomers via their intermediate stannylene acetals may thus be exploited to generate biologically active oligosaccharides for biomedical applications.

Solution conformation of methyl β-xylobioside from optical rotation

A recently developed semiempirical model of saccharide optical activity is used to calculate the Na(D) rotation of methyl β-xylobioside in solution as a function of its conformation. Combining the results with published conformational-energy calculations leads to a picture in which folded conformations, with either Φ or Ψ greater than 120°, make up no less than 40% of the total, in aqueous solution. This conclusion is consistent with an earlier analysis of the optical rotation of cellobiose in which folded forms were found to account for D rotation of methyl β-xylobioside in solution as a function of its conformation. Combining the results with published conformational-energy calculations leads to a picture in which folded conformations, with either φ or Ψ greater than 120°, make up no less 40% of the total, in aqueous solution. This conclusion is consistent with an earlier analysis of the optical rotation of cellobiose in which folded forms were found 10% of the total.

THE EFFECT OF REPLACING A 3-O-ACETYL GROUP BY A 3-O-BENZY; GROUP IN A METHYL 4-O-TRITYL-β-D-XYLOPYRANOSIDE DERIVATIVE ON THE EFFICIENCY OF 1,2-trans-GLYCOSYLATION WITH A D-XYLOSE 1,2-O-(1-CYANOETHYLIDENE) DERIVATIVE

Replacement of AcO-3 in methyl 2,3-di-O-acetyl-4-O-trityl-β-D-xylopyranoside with a benzyl group greatly increases the 1,2-trans-stereoselectivity of glycosylation with D-xylopyranose 1,2-O-(1-Cyanoethylidene) derivative.Anomerisation of methyl 2-O-benzyl-β-D-xylopyranoside derivatives occured under the action of triphenylmethylium perchlorate.

SEQUENTIAL SYNTHESIS AND (13)C-N.M.R. SPECTRA OF METHYL β-GLYCOSIDES OF (1->4)-β-D-XYLO-OLIGOSACCHARIDES

The reaction of 2,3-di-O-acetyl-4-O-benzyl-α,β-D-xylopyranosyl bromide (2) with methyl 2,3-di-O-acetyl-β-D-xylopyranoside gave methyl O-(2,3-di-O-acetyl-4-O-benzyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (22).Catalytic hydrogenolysis

SYNTHESIS OF A SERIES OF POSITIONALLY ISOMERIC METHYL O-(α- AND β-D-XYLOPYRANOSYL)-β-D-XYLOPYRANOSIDES

Crystalline α- and β-(1->2, 1->3 and 1->4)-linked methyl β-D-xylobiosides have been obtained by procedures based on condensation of 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide with positionally isomeric methyl di-O-acetyl-β-D-xylopyranosides, followed by deacetylation.Per-O-acetates of the isomeric methyl β-D-xylobiosides were also obtained crystalline.The β-linked disaccharide methyl glycosides, methylated on a preparative scale, gave crystalline fully methylated products