156917-53-2

Basic information

• Product Name: benzyl 4,6-O-isopropylidene-3-O-methyl-β-D-mannopyranoside
• CAS NO: 156917-53-2
• Molecular Weight: 324.374
• Mol File: 156917-53-2.mol

Chemical Properties

• CAS DataBase Reference: benzyl 4,6-O-isopropylidene-3-O-methyl-β-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 4,6-O-isopropylidene-3-O-methyl-β-D-mannopyranoside(156917-53-2)
• EPA Substance Registry System: benzyl 4,6-O-isopropylidene-3-O-methyl-β-D-mannopyranoside(156917-53-2)

Safety Data

• Hazardous Substances Data: 156917-53-2(Hazardous Substances Data)

Upstream product

• 156626-36-7 benzyl 4,6-O-isopropylidene-3-O-methyl-β-D-glucopyranoside 

Downstream Products

• 156917-54-3 benzyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-mannopyranoside 

Relevant articles and documents

Synthesis of three tetrasaccharides containing 3-O-methyl-D-mannose, as model compounds for xylose-containing carbohydrate chains from N-glycoproteins

The synthesis is reported of methyl 3,6-di-O-(3-O-methyl-α-D-mannopyranosyl)-2-O-β-D-xylopyranosyl-β-D-mannopyranoside (2), methyl 6-O-α-D-mannopyranosyl-3-O-(3-O-methyl-α-D-mannopyranosyl)-2-O-β-D-xylopyranosyl-β-D-mannopyranoside (3), and methyl 3-O-α-D-mannopyranosyl-6-O-(3-O-methyl-α-D-mannopyranosyl)-2-O-β-D-xylopyranosyl-β-D-mannopyranoside (4).The various methyl β-D-Man p acceptor derivatives were prepared from the corresponding methyl β-D-Glc p derivatives via oxidation-reduction.All glycosyl donors were coupled using the trichloroacetimidate method at -40 degC in dichloromethane with trimethylsilyl triflate as a catalyst.Methyl-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside (7) was condensed with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (8).Regioselective reductive 4,6-O-benzylidene ring-opening on the resulting disaccharide derivative, followed by acetylation, and hydrogenation gave methyl 4-O-acetyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside (12).Coupling of 12 with 2,4,6-tri-O-acetyl-3-O-methyl-α-D-mannopyranosyl trichloroacetimidate (18) afforded tetrasaccharide derivative 19, and subsequent O-deacetylation gave 2.Methyl 3-O-benzyl-4,6-O-prop-2-enylidene-β-D-mannopyranoside (22) was condensed with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (8).Regioselective reductive 4,6-O-prop-2-enylidene ring-opening on the resulting disaccharide derivative, followed by acetylation, and deallylation at O-6 gave methyl 4-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside (26-a), which was either condensed with 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroacetimidate (27) or 18, to give trisaccharide derivatives 28 or 31, respectively.Debenzylation of 28 followed by condensation with 18 gave, after O-deacetylation, 3, whereas debenzylation of 31 followed by condensation with 27 gave, after O-deacetylation, 4.