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

Uses

Octaacetyl-β-maltose is used to prepare self-reproducing micelles in the preparation of triazole-containing disaccharides. It has also been used as a reactant in the synthesis of neoglycoconjugates through glycosyl aldehydes featuring bioorthogonal oxime bond formation.

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

• 7343-99-9 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-nitro-phenoxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 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 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 14227-66-8 acetobromocellobiose 
• 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 
• 27894-92-4 p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 

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.