38166-65-3

Basic information

• Product Name: 3-Acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose
• Synonyms: 3-Acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose;1,2:5,6-Bis-O-(1-Methylethylidene)-α-D-galactofuranose Acetate
• CAS NO: 38166-65-3
• Molecular Formula: C₁₄H₂₂O₇
• Molecular Weight: 302.32028
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 38166-65-3.mol

Chemical Properties

• Boiling Point: 350.625°C at 760 mmHg
• Flash Point: 151.361°C
• Appearance: /
• Density: 1.253g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.502
• Solubility: Chloroform, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3-Acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose(38166-65-3)
• EPA Substance Registry System: 3-Acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose(38166-65-3)

Safety Data

• Hazardous Substances Data: 38166-65-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C14H22O7/c1-7(15)17-10-9(8-6-16-13(2,3)19-8)18-12-11(10)20-14(4,5)21-12/h8-12H,6H2,1-5H3/t8?,9-,10+,11?,12+/m0/s1

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-D-glucofuranoside 
• 79-20-9 acetic acid methyl ester 
• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 10534-59-5 tetrabutylammonium acetate 
• 19131-06-7 1,2:5,6-di-O-isoproylidene-3-O-tosyl-α-D-gulofuranose 

Downstream Products

• 109680-96-8 3-O-acetyl-1,2-O-isopropylidene-α-D-galactofuranose 
• 20689-03-6 1-((3aR,4S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 
• 582-52-5 diacetone glucose 
• 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 
• 109680-97-9 3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-α-D-galactofuranose 
• 109680-98-0 3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-β-L-arabino-hexofuranos-5-ulose 
• 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

A Novel Electrochemical Method of Acetylation of Alcohols by Methyl Acetate

A new electrochemical method of acetylation, using methyl acetate at room temperature, was developed.The current efficiency in all the reactions with primary alcohols exceeded 100 percent, ranging from 126 to 166 percent indicating that this method of acetylation is advantageous for the preparation of acetates from the viewpoint of energy economy.Keywords--acetic acid methyl ester; acetylation; alcoholysis; electrochemical reduction; transesterification; alcoholate anion

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.

L-Glucose. A convenient synthesis from D-glucose

L-Glucose has been synthesized from D-glucose by a convenient method involving methyl 2,3-O-isopropylidene-β-D-gulofuranosiduronic acid (6) as a key intermediate.Compound 6 was converted into L-glucono-1,5-lactone (8), which, by a selective reduction, afforded L-glucose (9).