496924-55-1

Basic information

• Product Name: alpha-D-Galactopyranose, 1-acetate (9CI)
• Synonyms: alpha-D-Galactopyranose, 1-acetate (9CI);1-O-Acetyl-a-D-galactopyranose - min 90% alpha
• CAS NO: 496924-55-1
• Molecular Formula: C8H14O7
• Molecular Weight: 222.19256
• Product Categories: ALCOHOL
• Mol File: 496924-55-1.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: alpha-D-Galactopyranose, 1-acetate (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-D-Galactopyranose, 1-acetate (9CI)(496924-55-1)
• EPA Substance Registry System: alpha-D-Galactopyranose, 1-acetate (9CI)(496924-55-1)

Safety Data

• Hazardous Substances Data: 496924-55-1(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 507-09-5 tiolacetic acid 
• 530-26-7 D-Mannose 
• 10257-28-0 D-Galactose 
• 123-54-6 acetylacetone 
• 75-36-5 acetyl chloride 
• 76939-53-2 α-D-glucosyl-1-phosphate 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 57-50-1 Sucrose 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 90358-01-3 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 
• 56822-48-1 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 

Relevant articles and documents

Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates

2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.

Selective anomeric acetylation of unprotected sugars in water

High yielding selective acetylation of only the anomeric hydroxyl of unprotected sugars is possible in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), thioacetic acid, and a suitable base. The reaction, which may be performed on a multi-gram scale, is stereoselective for sugars that possess a hydroxyl group at position-2, exclusively yielding the 1,2-trans products. The use of an iterative reagent addition procedure allows the use of sodium carbonate as the base, avoiding the formation of triethylammonium salts, which may hamper product purification. The glycosyl acetate products may be used as donor substrates for glycosidase-catalysed synthesis. The crude aqueous acetylation reaction mixture may also be used for this purpose.

Monosaccharidic mimetics of the sialyl LewisX tetrasaccharide based on 2,7-dihydroxynaphthalene

A potential monosaccharidic mimetic of the sialyl LewisX tetrasaccharide (sLeX) was identified based on an in silico docking study using the crystal structure of an E-selectin-sLeX complex. The chemical synthesis of the mimetic in an ortho-selective C-glycosylation is described. This compound and two close analogues were evaluated in a cell-based selectin binding assay where none of the tested mimetics showed an IC 50 below 1mM. This result can be explained by an unexpected 1C4 conformation of the mannosyl residue which precludes the required binding of the Ca2+-ion in E-selectin.