109680-96-8

Basic information

• Product Name: 3-Acetyl-1,2-O-isopropylidene-α-D-galactofuranose
• Synonyms: 3-Acetyl-1,2-O-isopropylidene-α-D-galactofuranose;1,2-O-(1-Methylethylidene)-α-D-galactofuranose 3-Acetate
• CAS NO: 109680-96-8
• Molecular Formula: C₁₁H₁₈O₇
• Molecular Weight: 262.25642
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 109680-96-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3-Acetyl-1,2-O-isopropylidene-α-D-galactofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyl-1,2-O-isopropylidene-α-D-galactofuranose(109680-96-8)
• EPA Substance Registry System: 3-Acetyl-1,2-O-isopropylidene-α-D-galactofuranose(109680-96-8)

Safety Data

• Hazardous Substances Data: 109680-96-8(Hazardous Substances Data)

Usage

Chemical Properties

Oil

Upstream product

• 19131-06-7 1,2:5,6-di-O-isoproylidene-3-O-tosyl-α-D-gulofuranose 
• 38166-65-3 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 17225-57-9 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose 
• 98032-70-3 Acetic acid (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Downstream Products

• 109681-00-7 5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-α-D-galactofuranose 
• 109681-01-8 5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-β-L-altrofuranose 
• 109680-99-1 Acetic acid (3aR,5S,6S,6aR)-5-{1-[(Z)-hydroxyimino]-2-trityloxy-ethyl}-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 109680-98-0 3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-β-L-arabino-hexofuranos-5-ulose 
• 714967-48-3 3-O-acetyl-5-azido-5-deoxy-1,2-O-isopropylidene-6-O-trityl-β-L-altrofuranose 
• 714967-55-2 3,6-di-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-(N'-phenylureido)-β-L-altrofuranose 
• 714967-52-9 5-deoxy-1,2-O-isopropylidene-5-(N'-phenylthioureido)-β-L-altrofuranose 
• 848310-71-4 (4-nitro)phenyl 2,3,5,6-tetra-O-acetyl-α-L-altrofuranoside 
• 848310-02-1 (4-nitro)phenyl α-L-altrofuranoside 

Relevant articles and documents

Non-natural aldofuranosides as substrates of a β-glucosidase

Based on glycosidase inhibitory activities of some known 1,4-iminoalditols, four aldofuranosides, (4-nitro)phenyl β-d-glucofuranoside, -β-d-galactofuranoside, -α-l-idofuranoside and -α-l- altrofuranoside, were identified as possible substrates of glucosid

A Simple and Facile Chemo- and Regioselective Deprotection of Acetonides Using Silica Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst

Silica supported sodium hydrogen sulfate (NaHSO4·SiO 2) has been found to be an efficient heterogeneous catalyst for chemo- and regioselective deprotection of acetonides at room temperature to produce the corresponding diols in excellent yields.

Synthesis of 5-amino-5-deoxy-D-galactopyranose and 1,5-dideoxy-1,5-imino-D-galactitol, and their inhibition of alpha- and beta-D-galactosidases.

A 12-step route is presented starting from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose for the preparation of the title compounds and their L-altro analogues. Their synthesis is based on the reduction with Raney nickel of a protected 5-hydroxyimino derivative of L-arabino-hexofuranos-5-ulose, with the following improvements for the preparation of a D-galactofuranose derivative: oxidation at C-3 with pyridinium dichromate-acetic anhydride, stereospecific reduction of a 3-O-acetyl-hex-3-enofuranose intermediate to the D-gulo derivative, and inversion at C-3 of its 3-tosylate with tetrabutylammonium acetate in chlorobenzene. alpha-D-Galactosidase from coffee beans and from Escherichia coli and beta-D-galactosidase from E. coli and Aspergillus wentii were inhibited with Ki values that ranged from 0.0007 to 8.2 microM. Formation of the enzyme-inhibitor complexes with the D-galactose analogue was on the time-scale of minutes, whereas the D-galactitol analogue showed a slow approach to the inhibition only with alpha-D-galactosidase from coffee beans and beta-D-galactosidase from A. wentii. N-Alkylation of the D-galactitol analogue was detrimental to the inhibition except for beta-D-galactosidase from E. coli and beta-D-glucosidase from almonds, but, even with these enzymes, the observed affinity enhancements were 10(2) to 10(3)-times smaller than those of N-alkylated D-galactosylamine and D-glucosylamine.