105444-14-2

Basic information

• Product Name: 1',2,3,4,4',6,6'-hepta-O-acetylsucrose
• Synonyms: 1',2,3,4,4',6,6'-hepta-O-acetylsucrose
• CAS NO: 105444-14-2
• Molecular Weight: 636.561
• Mol File: 105444-14-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1',2,3,4,4',6,6'-hepta-O-acetylsucrose(CAS DataBase Reference)
• NIST Chemistry Reference: 1',2,3,4,4',6,6'-hepta-O-acetylsucrose(105444-14-2)
• EPA Substance Registry System: 1',2,3,4,4',6,6'-hepta-O-acetylsucrose(105444-14-2)

Safety Data

• Hazardous Substances Data: 105444-14-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 102069-21-6 2,3,4,6,1',6'-hexa-O-acetylsucrose 

Relevant articles and documents

STRUCTURE OF PENTA-O-ACETYLSUCROSES FORMED BY DEACETYLATION OF OCTA-O-ACETYLSUCROSE. REACTION OF 2,3,4,6,6'-PENTA-O-ACETYLSUCROSE

Chromatographic separation of penta-O-acetylsucrose fraction from deacetylation of octa-O-acetylsucrose by treatment with aluminum oxide impregnated by potassium carbonate gave-1',3,4,6,6'-penta-O-acetylsucrose (XII), 1,2,3,4,6-penta-O-acetylsucrose (XIII), and the prevailing-2,3,4,6,6'-penta-O-acetylsucrose (XIV).Reaction of compound XIV with two equivalents of p-toluenesulfonyl chloride in pyridine produced besides the 1'-O-p-toluenesulfonyl derivative XXI and 1',3',4'-tri-O-tosyl derivative XXII also 1',3'-di-O-tosyl derivative XXIII and 1',4'-di-O-tosyl derivativeXX. 1',2-anhydro(3,4,6-tri-O-acetyl-α-D-glucopyranosyl 6'-O-acetyl-3',4'-anhydro-β-D-ribo-hexulofuranoside) (X) and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-β-D-ribo-hexulofuranoside (VIII) were prepared from compound XXIII by two minutes boiling with 1M sodium methoxide, evaporation of the reaction mixture, and acetylation (method A).Compound XX gives under reaction conditions of method A 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-β-D-lyxo-hexulofuranoside (IX) only.However, upon 24 h boiling with 1M sodium methoxide, neutralization, evaporation, and acetylation of the reaction mixture (method B), we obtained 3,3',4,6,6'-penta-O-acetyl-1',2-anhydro-4'-O-methylsucrose (XXIV), 1',2,3,3',4,6,6'-hepta-O-acetyl-4'-O-methylsucrose (XXV), and 1',2-anhydro-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl 3',4',6'-tri-O-acetyl-β-D-xylo-hexulofuranoside) (XXVI).Compounds XXV and XXVI are also formed by reaction of epoxide IX with sodium methoxide according to method B.Compound XXVI can be prepared by hydrolysis of the dianhydro derivative X followed by acetylation.A reaction mechanismfor compound XXVI formation from the epoxide IX is proposed.It assumes an intramolecular opening of the oxirane ring in compound IX under formation of α-D-glucopyranosyl 1,3-anhydro-β-D-xylo-hexulofuranoside (XLVI).The 1'-O-tosyl derivative XXI reacts with sodium methoxide according to method B to give 3,3',4,4',6,6'-hexa-O-acetyl-1',2-anhydrosucrose (XXVIII), octa-O-acetylsucrose, and 2,3,3',4,6,6'-hexa-O-acetyl-1',4'-anhydrosucrose XL.