28235-34-9

Basic information

• Product Name: Tri-O-acetyl-1,6-anhydro-idopyranose
• CAS NO: 28235-34-9
• Molecular Weight: 288.254
• Mol File: 28235-34-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Tri-O-acetyl-1,6-anhydro-idopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: Tri-O-acetyl-1,6-anhydro-idopyranose(28235-34-9)
• EPA Substance Registry System: Tri-O-acetyl-1,6-anhydro-idopyranose(28235-34-9)

Safety Data

• Hazardous Substances Data: 28235-34-9(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 81969-64-4 1,6-Anhydro-α-L-idohexofuranose 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 2592-44-1 3-O-acetyl-1,2-O-isopropylidene-5,6-O-di-toluene-p-sulphonyl-α-D-glucofuranose 
• 55263-78-0 1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone 
• 4056-11-5 5-azido-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-glucofuranose 
• 30694-77-0 3,6-di-O-acetyl-1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranose 
• 63-29-6 D-glucurono-6,3-lactone 
• 60619-47-8 1,6-anhydro-β-L-idopyranose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 
• 89157-91-5 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant articles and documents

Re-examination of the acid hydrolysis of 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose

-

SYNTHESIS OF SOME ARYL 2,3,4,6-TETRA-O-ACETYL-L-IDOPYRANOSIDES AND OF 4-METHYLCOUMARIN-7-YL α-L-IDOPYRANOSIDURONIC ACID

Several routes for synthesis of 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose have been evaluated.Previously described routes, which involved selective sulphonylation, were not reproducible on a 100-g scale.To overcome this difficulty, a new variation was developed, involving complete tosylation of 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone followed by reduction and acetylation.The idofuranose derivative was converted into the desired 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose via 1,6-anhydro-β-L-idopyranose.Fusion of 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose with 4-nitrophenol, 1- or 2-naphtol, or 4-methylcoumarin-7-ol, using freshly fused zinc chloride as catalyst, gave an anomeric mixture of glycosides, with the α anomer being preponderant.The major 4-methylcoumarin-7-yl glycoside was deacylated and converted, by catalytic oxidation, into 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid, fluorogenic substrate for α-L-iduronidase.

Syntheses with partially benzylated sugars. IX. Synthesis of a 5-hexulosonic acid (5-ketohexonic acid) derivative and inversion of configuration at C-5 in an aldose.

-