14199-54-3

Basic information

• Product Name: 2-O-Methyl-β-D-glucopyranose tetraacetate
• Synonyms: 2-O-Methyl-β-D-glucopyranose tetraacetate
• CAS NO: 14199-54-3
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.32918
• Mol File: 14199-54-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-O-Methyl-β-D-glucopyranose tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-O-Methyl-β-D-glucopyranose tetraacetate(14199-54-3)
• EPA Substance Registry System: 2-O-Methyl-β-D-glucopyranose tetraacetate(14199-54-3)

Safety Data

• Hazardous Substances Data: 14199-54-3(Hazardous Substances Data)

Upstream product

• 10257-28-0 D-Galactose 
• 108-24-7 acetic anhydride 
• 2774-19-8 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 65877-23-8 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside 
• 64605-18-1 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside 
• 27552-08-5 methyl 2-O-methyl-α-D-mannopyranoside 

Downstream Products

• 1402142-45-3 2-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyloxy)acetaldehyde 
• 1402142-33-9 (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 1402142-32-8 (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 1402142-35-1 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose 
• 1402142-39-5 4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose 
• 2595-07-5 allyl β-D-galactopyranoside 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 60478-61-7 allyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 10343-15-4 allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 10357-29-6 p-nitrophenyl 2-O-methyl-α-D-mannopyranoside 
• 10357-33-2 p-nitrophenyl 3,4,6-tri-O-acetyl-2-O-methyl-α-D-mannopyranoside 

Relevant articles and documents

Synthesis of trisaccharides by hetero-diels-alder welding of two monosaccharide units

A new strategy for the synthesis of di- and trisaccharides based on the de novo synthesis of the linking saccharide unit is presented. In this strategy, functionalized monosaccharide building blocks already incorporating the glycosidic linkages are welded together using a metal-catalyzed hetero-Diels-Alder (HDA) reaction to generate a new monosaccharide unit between them. The highest yields and selectivities in the HDA reaction were obtained by using chiral Schiff base chromium complexes. Disaccharide products were accessible by reaction of Danishefsky's diene with acetyl- and benzyl-protected galactoside aldehydes. For the synthesis of trisaccharide products, acetyl-protected glucose or galactose-derived dienes were fused with monosaccharide-derived aldehydes using chromium catalysts for the HDA reaction. The desired trisaccharide products were obtained in moderate to good yields with excellent stereoselectivity. The central pyranulose-ring generated in the process possessed an L-cis-enulose configuration according to NMR spectroscopy and modeling studies. 1 + 1 equals 3! The hetero-Diels-Alder union of two functionalized monosaccharide building blocks - one bearing an aldehyde and the other a readily accessible diene moiety - affords functionalized trisaccharide structures in moderate to good yields and excellent stereoselectivities when β-anomers of the aldehydes are used. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Synthesis of monomethyl derivatives of p-nitrophenyl α-d-gluco, galacto, and mannopyranosides and their hydrolytic properties against α-glycosidases

All possible monomethyl derivatives of p-nitrophenyl α-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of α-glucosidase (rice), α-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and α-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea α-galactosidase and the almond and jack bean α-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, rice α-glucosidase and green coffee bean and A. niger α-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.