28868-67-9

Basic information

• Product Name: Maltosan Hexaacetate
• Synonyms: Maltosan Hexaacetate;2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-beta-D-maltose;2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-b-D-maltose
• CAS NO: 28868-67-9
• Molecular Formula: C₂₄H₃₂O₁₆
• Molecular Weight: 576.5013
• Product Categories: Carbohydrates & Derivatives
• Mol File: 28868-67-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 603.2°C at 760 mmHg
• Flash Point: 254.3°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 1.67E-14mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: Maltosan Hexaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Maltosan Hexaacetate(28868-67-9)
• EPA Substance Registry System: Maltosan Hexaacetate(28868-67-9)

Safety Data

• Hazardous Substances Data: 28868-67-9(Hazardous Substances Data)

Usage

Uses

Maltosan Hexaacetate, used in the synthesis of potential antimicrobial agents from maltose, a pseudodisaccharides containing aminocyclitols as constituent.

InChI:InChI=1/C24H32O16/c1-9(25)31-7-15-17(33-10(2)26)19(34-11(3)27)22(37-14(6)30)24(39-15)40-18-16-8-32-23(38-16)21(36-13(5)29)20(18)35-12(4)28/h15-24H,7-8H2,1-6H3

Upstream product

• 108-24-7 acetic anhydride 
• 6983-27-3 1,6-anhydro-β-maltose 
• 33600-53-2 ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltoside 
• 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 
• 115414-31-8 4-chlorophenyl 2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-maltoside 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 3616-19-1 lactose octaacetate 
• 440-02-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 
• 77110-60-2 Pentachlorophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 115414-32-9 Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-acetoxymethyl-2-(4-chloro-benzenesulfonyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 27891-93-6 phenyl maltosyl sulfone heptaacetate 
• 115431-22-6 Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-acetoxymethyl-2-ethanesulfonyl-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 77987-41-8 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone 
• 130155-18-9 phenyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-6-deoxy-1-thio-β-D-xylo-hexo-5-enopyranoside 
• 130130-54-0 Acetic acid (2S,3R,4S,5S,6S)-3-acetoxy-6-iodomethyl-2-phenylsulfanyl-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 130130-53-9 phenyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-6-O-(p-tolylsulphonyl)-1-thio-β-D-glucopyranoside 
• 28810-02-8 O¹,O²,O³-triacetyl-O⁴-(tetra-O-acetyl-α-D-glucopyranosyl)-O⁶-(toluene-4-sulfonyl)-β-D-glucopyranose 
• 28810-03-9 1,2,3-tri-O-acetyl-6-deoxy-6-iodo-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose 
• 6983-27-3 1,6-anhydro-β-maltose 
• 130130-43-7 1,6-anhydro-2,3-di-O-benzoyl-4',6'-O-benzylidene-2',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-maltose 
• 130515-42-3 2,2',3,3',4',6'-hexa-O-acetyl-1-thio-β-maltoside 
• 130130-52-8 phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 744-05-8 methyl beta-D-maltoside 

Relevant articles and documents

EFFECT OF PROTECTING GROUPS AND SOLVENTS IN ANOMERIC O-ALKYLATION OF MANNOPYRANOSE

Anomeric O-alkylation of mannopyranoses with various protecting groups was investigated using mannose derivatives and 2,3-O-isopropylidene-1-O-trifluoromethanesulfonyl-D-glycerol (1) as alkylating agent.Generally, in polar solvents higher α/β ratios were obtained than in nonpolar solvents.Sterically demanding protecting groups at the 6-O-position and polar solvents led to higher yields.Reactivity differences were explained by different complex formation.Based on these results mannopyranosyl-α(1-4)glucopyranosides 26 and 27 were synthesized using mannose derivatives 5 and 6 having a 6-O-(p-methoxyphenyl)diphenylmethyl group and galactosyl trifluoromethanesulfonate 24 or nonafluorobutanesulfonate (nonaflate) 25, respectively, as alkylating agents.

Synthesis of 6-(S) Deuterium-Labelled Derivatives of Maltose and Isomaltose

The 6-(S) deuterium-labelled compounds methyl β-isomaltoside (4a), methyl β-maltoside (8a) and methyl 4,6-di-O-(α-D-glucopyranosyl)-β-D-glucopyranoside (12) have been synthesized from deuterium-substituted 1,6-anhydro compounds.The 6-(R) deuterium-labelled compound methyl β-maltoside (10) has been prepared by inversion at the 6-position of the corresponding 6-(S) derivative.The compounds have all been examined by (1)H NMR spectroscopy at 500 MHz and their preferred solution conformation has been inferred from the J56R and J56S coupling constants.

A modified procedure for the synthesis of 1,6-anhydro disaccharides

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