32447-71-5

Basic information

• Product Name: maltal
• Synonyms: maltal;4-O-α-D-Glucopyranosyl-1,5-anhydro-2-deoxy-D-arabino-hexa-1-enitol
• CAS NO: 32447-71-5
• Molecular Formula: C₁₂H₂₀O₉
• Molecular Weight: 308.2818
• Mol File: 32447-71-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 612°Cat760mmHg
• Flash Point: 323.9°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 1.55E-17mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: maltal(CAS DataBase Reference)
• NIST Chemistry Reference: maltal(32447-71-5)
• EPA Substance Registry System: maltal(32447-71-5)

Safety Data

• Hazardous Substances Data: 32447-71-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H20O9/c13-3-6-8(16)9(17)10(18)12(20-6)21-11-5(15)1-2-19-7(11)4-14/h1-2,5-18H,3-4H2/t5-,6-,7-,8-,9+,10-,11+,12-/m1/s1

Upstream product

• 51450-24-9 hexa-O-acetyl-D-maltal 
• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 

Downstream Products

• 1353094-10-6 C₆₀H₅₉NO₁₀ 

Relevant articles and documents

From 1,4-Disaccharide to 1,3-Glycosyl Carbasugar: Synthesis of a Bespoke Inhibitor of Family GH99 Endo-α-mannosidase

Understanding the enzyme reaction mechanism can lead to the design of enzyme inhibitors. A Claisen rearrangement was used to allow conversion of an α-1,4-disaccharide into an α-1,3-linked glycosyl carbasugar to target the endo-α-mannosidase from the GH99 glycosidase family, which, unusually, is believed to act through a 1,2-anhydrosugar "epoxide" intermediate. Using NMR and X-ray crystallography, it is shown that glucosyl carbasugar α-aziridines can act as reasonably potent endo-α-mannosidase inhibitors, likely by virtue of their shape mimicry and the interactions of the aziridine nitrogen with the conserved catalytic acid/base of the enzyme active site.

Base-catalyzed degradation of permethylated 3-O-glycosylglycopyranosid-2-uloses

In a modification of the Svensson degradation, otherwise permethylated glycopyranosid-2-uloses bearing 4-O-glycosyl substituents are formed by the Swern oxidation. Base-catalyzed elimination on treatment with triethylamine then gives 4-deoxy-3-O-methylglyc-3-enopyranosid-2-ulose-terminated oligosaccharides with liberation of glycosyl substituents as reducing sugars but without further degradation. Mild acid hydrolysis results in removal of the unsaturated sugar residues so that the overall depolymerization occurs with net loss of the initially oxidized sugar residue. In a modification of the Svensson degradation, otherwise permethylated glycopyranosid-2-uloses bearing 4-O-glycosyl substituents are formed by the Swern oxidation. Base-catalyzed elimination on treatment with triethylamine then gives 4-deoxy-3-O-methylglyc-3-enopyranosid -2-ulose-terminated oligosaccharides with liberation of glycosly substituents as reducing sugars but without further degradation. Mild acid hydrolysis results in removal of the unsaturated sugar residues so that the overall depolymerization occurs with net loss only of the initially oxidized sugar residue.