22352-19-8

Basic information

• Product Name: Octaacetyl-beta-maltose
• Synonyms: OCTA-O-ACETYL-BETA-D-MALTOSE;Octaacetyl-beta-maltose;OCTAACETYL MALTOSE;1,2,2',3,3',4',6,6'-OCTA-O-ACETYL-BETA MALTOSE;4-O-(2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranose tetraacetate;MALTOSE OCTAACETATE;beta-d-maltopyranose octaacetate;BETA-D-MALTOSE OCTAACETATE
• CAS NO: 22352-19-8
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.59
• EINECS: 606-994-8
• Product Categories: Carbohydrates;Carbohydrates A to;Carbohydrates M-OBiochemicals and Reagents;Polysaccharide
• Mol File: 22352-19-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 159-160°C
• Boiling Point: 683.055 °C at 760 mmHg
• Flash Point: 281.178 °C
• Appearance: /
• Density: 1.37
• Vapor Pressure: 1.64E-18mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: −20°C
• BRN: 79279
• CAS DataBase Reference: Octaacetyl-beta-maltose(CAS DataBase Reference)
• NIST Chemistry Reference: Octaacetyl-beta-maltose(22352-19-8)
• EPA Substance Registry System: Octaacetyl-beta-maltose(22352-19-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22352-19-8(Hazardous Substances Data)

Usage

Description

Octaacetyl-beta-maltose is a derivative of beta-maltose, a disaccharide composed of two glucose units, where all eight hydroxyl groups are acetylated. This modification enhances its stability and reactivity in various chemical processes.

Uses

Used in Pharmaceutical Industry:
Octaacetyl-beta-maltose is used as a reactant for the preparation of self-reproducing micelles in the synthesis of triazole-containing disaccharides. These micelles have potential applications in drug delivery systems, offering targeted and controlled release of therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, Octaacetyl-beta-maltose is utilized as a reactant for the synthesis of neoglycoconjugates through glycosyl aldehydes featuring bioorthogonal oxime bond formation. This allows for the creation of complex carbohydrate structures with potential applications in biochemistry and medicinal chemistry, such as the development of new drugs and vaccines.

InChI:InChI=1/C28H38O19/c1-11(29)37-9-19-21(39-13(3)31)23(40-14(4)32)26(43-17(7)35)28(46-19)47-22-20(10-38-12(2)30)45-27(44-18(8)36)25(42-16(6)34)24(22)41-15(5)33/h19-28H,9-10H2,1-8H3/t19-,20-,21-,22-,23+,24+,25-,26-,27-,28-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 134-96-3 syringic aldehyde 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 99337-73-2 1,2,3,6-tetra-O-acetyl-4-O-trityl-β-D-glucopyranose 
• 127066-70-0 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate 

Downstream Products

• 125471-64-9 2-O-benzyl-1,3-bis-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)glycerol 
• 125471-65-0 3-O-acetyl-2-O-benzyl-1-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)-(R,S)-glycerol 
• 160227-12-3 4-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 67310-53-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 30854-62-7 lactosyl azide 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 33012-49-6 1-azido-1-deoxy-4-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucose 
• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 
• 29019-41-8 p-Tolyl O-(2,3,4,6,-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 5160-10-1 2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide 
• 92052-38-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 
• 106256-89-7 (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 

Relevant articles and documents

Synthesis of aryl glycosides as vir gene inducers of Agrobacterium tumefaciens

Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated. Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated.