108739-88-4

Basic information

• Product Name: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL FORMAMIDE
• Synonyms: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL FORMAMIDE;2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosylformamide;2,3,4,6-TETRA-O-ACETYL-SS-D-GALACTOPYRANOSYL FORMAMIDE
• CAS NO: 108739-88-4
• Molecular Formula: C₁₅H₂₁NO₁₀
• Molecular Weight: 375.32794
• Mol File: 108739-88-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL FORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL FORMAMIDE(108739-88-4)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL FORMAMIDE(108739-88-4)

Safety Data

• Hazardous Substances Data: 108739-88-4(Hazardous Substances Data)

Usage

Derivative of beta-D-galactopyranose

A type of sugar

Usage

Synthesis of glycosides and glycosylamides

Potential applications

Pharmaceutical and food industries

Property

Ability to modify the properties of biologically active molecules

Common use

Reagent in organic and medicinal chemistry research

Upstream product

• 52443-07-9 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile 
• 1313-13-9 manganese dioxide 

Downstream Products

• 108672-06-6 diazomethyl β-D-galactopyranosyl ketone 
• 502186-10-9 pentachlorophenyl 3,4,5,7-tetra-O-acetyl-2-bromo-2-deoxy-α-D-galacto-hept-2-ulopyranosonate 
• 502186-07-4 pentachlorophenyl 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonate 
• 159895-07-5 C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-galactopyranosyl)formamide 

Relevant articles and documents

Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

[RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixture

Process for the preparation of (+)-hydantocidin and analogs thereof

Hydantocidin is a potent non-selective herbicidal natural product. This invention provides an efficient method for the enantioselective preparation of (+)-hydantocidin, analogs thereof and intermediates therefor.

N-Substituted (β-D-galactopyranosylmethyl)amines, and C-β-D-galactopyranosylformamides, and related compounds

A series of N-substituted (β-D-galactopyranosylmethyl)amines, a series of N-substituted C-β-D-galactopyranosylformamides, and other C-β-D-galactopyranosyl compounds have been synthesized and characterized.Most were prepared from β-D-galactopyranosyl cyanide via C-β-D-galactopyranosylformic acid.

SYNTHESIS OF DIAZOMETHYL β-D-GALACTOPYRANOSYL AND β-D-GLUCOPYRANOSYL KETONES. POTENTIAL AFFINITY-LABELING REAGENTS FOR CARBOHYDRATE-BINDING PROTEINS

3,7-Anhydro-1-deoxy-1-diazo-D-glycero-L-manno-2-octulose (6a; diazomethyl β-D-galactopyranosyl ketone) and 3,7-anhydro-1-deoxy-1-diazo-D-glycero-D-gulo-2-octulose (6b; diazomethyl β-D-glucopyranosyl ketone) have been prepared.Readily available C-glycosyl compounds possessing the appropriate stereochemistry and hydroxyl-group protection, viz., per-O-acetyl-2,6-anhydroheptononitriles and per-O-acetyl-2,6-anhydroheptonamides, were employed as precursors to per-O-acetyl-2,6-anhydroheptonic acids.These key intermediates were then converted into mixed carboxylic-carbonic acid anhydrides, and these caused to react with diazomethane, to give the corresponding per-O-acetyl-3,7-anhydro-1-deoxy-1-diazo-2-octuloses.Zemplen deacetylation gave, stereospecifically, the crystalline target-molecules in good overall yield.It is proposed that such C-glycosyl compounds as 6a and 6b, which possess the diazoacetyl functional group as their "aglycon", will be useful as enzyme-activated irreversible inhibitors (suicide substrates) of glycosidases, and as photoaffinity-labeling reagents and classical affinity-labeling reagents for carbohydrate-binding proteins.