10535-09-8

Basic information

• Product Name: 1,2,3,5,6-penta-O-acetylhexofuranose
• Synonyms: 1,2,3,5,6-Penta-O-acetylhexofuranose
• CAS NO: 10535-09-8
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.3393
• Mol File: 10535-09-8.mol

Chemical Properties

• Boiling Point: 460.3°C at 760 mmHg
• Flash Point: 200.2°C
• Density: 1.3g/cm³
• Vapor Pressure: 1.17E-08mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: 1,2,3,5,6-penta-O-acetylhexofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5,6-penta-O-acetylhexofuranose(10535-09-8)
• EPA Substance Registry System: 1,2,3,5,6-penta-O-acetylhexofuranose(10535-09-8)

Safety Data

• Hazardous Substances Data: 10535-09-8(Hazardous Substances Data)

Usage

Derivative of hexofuranose

1,2,3,5,6-penta-O-acetylhexofuranose is a chemical compound that is derived from hexofuranose, a six-carbon sugar molecule.

Used in organic synthesis

It is broadly used in organic synthesis for the preparation of various types of carbohydrates and related compounds.

Protective group

1,2,3,5,6-penta-O-acetylhexofuranose is used as a protective group in carbohydrate chemistry, which can be selectively removed under mild conditions.

Employed in the synthesis of complex natural products and pharmaceuticals

It is commonly employed in the synthesis of complex natural products and pharmaceuticals.

Confers chemical properties

The acetyl groups on the hexofuranose molecule confer certain chemical properties that make it useful in a variety of chemical reactions and applications.

Important intermediate

1,2,3,5,6-penta-O-acetylhexofuranose is an important intermediate in the synthesis of carbohydrates and other biologically active compounds.

Upstream product

• 59-23-4 D-Galactose 
• 108-24-7 acetic anhydride 
• 10257-28-0 D-Galactose 
• 563-63-3 silver(I) acetate 
• 64-19-7 acetic acid 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 543-80-6 barium(II) acetate 

Downstream Products

• 282088-49-7 phenyl 2,3,5,6-tetra-O-acetyl-β-D-selenogalactofuranoside 
• 39698-24-3 tetra-O-acetyl-β-D-galactofuranosyl bromide 
• 882512-95-0 ethyl (2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-(1->3)-4,6-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 328046-75-9 ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-2,3-di-O-benzyl-β-D-galactofuranoside 
• 328046-74-8 acetic acid 4-acetoxy-2-[2-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-(3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethoxy]-5-(1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester 
• 352463-50-4 ethyl 5-O-(β-D-galactofuranosyl)-2,3,6-tri-O-benzyl-β-D-galactofuranoside 
• 352463-49-1 Acetic acid (2R,3R,4S,5S)-4-acetoxy-2-[(R)-2-benzyloxy-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethoxy]-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester 
• 107691-62-3 Allyl 2,3-O-dibenzyl-β-D-galactofuranoside 
• 107691-61-2 Allyl 2,3-O-dibenzyl-5,6-O-isopropyliden-β-D-galactofuranoside 
• 107691-63-4 Allyl 2,3,6-tri-O-benzyl-β-D-galactofuranoside 
• 107691-66-7 Allyl 2,3,6-tri-O-benzyl-5-O-β-D-galactofuranosyl-β-D-galactofuranoside 
• 107691-65-6 Allyl 2,3,6-tri-O-benzyl-5-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-β-D-galactofuranoside 
• 107724-09-4 Allyl 2,3,6-tri-O-benzyl-5-O-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl)-β-D-galactofuranosid 

Relevant articles and documents

Synthesis of immunostimulatory α- C -galactosylceramide glycolipids via sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate- mediated epoxide opening

Stereocontrolled syntheses of α-C-GalCer (2) and its α-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and d-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et2AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.

The influence of boric acid on the acetylation of aldoses: 'One-pot' syntheses of penta-O-acetyl-β-D-glucofuranose and its crystalline propanoyl analogue

When glucose and boric acid are heated in acetic acid a soluble compound forms from which, with acetic anhydride and catalytic amounts of sulfuric acid, a mixture consisting of >90% of the glucofuranose per-acetates (α : β ratio 1 : 1.8) is obtained in high yield. In the absence of the sulfuric acid partial acetylation takes place and penta-O-acetyl-β-D-glucofuranose (α: β ratio 1 : 52) is obtainable in good yield by removal of boric acid and completion of the esterification by addition of acetic anhydride and pyridine. A new, crystalline glucofuranose, penta-O-propanoyl-β-D-glucofuranose, is obtained in 58% yield in a 'one-pot' procedure using boric acid. The effects of boric acid on the acid-catalysed acetylation of other aldo-hexoses and -pentoses suggest that the synthesis of furanosyl per-esters could be successful with xylose and idose as well as with glucose.

H-Beta zeolite as an efficient catalyst for per-O-acetylation of mono- and disaccharides

Among the six different zeolites examined, H-beta is demonstrated to be a highly efficient and selective catalyst for the per-O-acetylation of various mono-and disaccharides and methyl glycosides.