5349-08-6

Usage

Structure

Triacetate derivative of a bicyclic ether

Usage

Solvent, plasticizer, reagent in chemical synthesis

Physical properties

Colorless, odorless liquid, high boiling point

Stability

Stable under normal conditions

Safety concerns

Potential health and safety risks if not used properly

Upstream product

• 108-24-7 acetic anhydride 
• 81969-64-4 1,6-Anhydro-α-L-idohexofuranose 
• 59-23-4 D-Galactose 
• 118475-44-8 1,6-Anhydro-2,3-di-O-benzyl-α-D-galactofuranose 
• 259826-50-1 1,6-anhydro-2,3,5-tri-O-benzoyl-α-D-galactofuranose 
• 33818-21-2 1,6-Anhydro-α-D-galactofuranose 
• 29388-46-3 methyl 2,3-di-O-benzyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

An efficient method for the synthesis of a 1,6-anhydro-α-D-galactofuranose derivative and its application in the synthesis of oligosaccharides

Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-β-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactofuranoside (1). The anhydro compound 3 was converted to the

α-Glucosidase Inhibitors, 6. - Synthesis of 1,6-Anhydro-D-glucose and -D-galactose Derivatives - Preparation of 1-Deoxynojirimycin

Methyl 2,3-di-O-benzyl-D-glucopyranoside (2) is transformed in the presence of p-toluenesulfonic acid and 2,2,2-trichloro- or 2,2,2-trifluoroethanol into the 4-O-unprotected 1,6-anhydropyranose 4.The amount of 1,6-anhydrofuranose 5, formed as a byproduct of this reaction, can be increased by longer reaction times.Similarly, from methyl 2,3-di-O-benzyl-D-galactopyranoside (9) the corresponding 1,6-anhydro compounds 10 and 12 were obtained. 1-Deoxynojirimycin (31) is obtained from the 5-O-unprotected 1,6-anhydroglucofuranose 5 in a few steps.The stereoselectiveintroduction of nitrogen at C-5 is reached by inversion of the configuration of the 5-OH group through oxidation and reduction and subsequent triflate activation for the invertive azide group introduction

1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose

The title compound 13 is prepared on different routes from suitable benzyl derivatives with gluco-configuration.Preparations use the susceptibility of axial 5-O-benzyl groups in this compounds to selective hydrogenolysis, thus allowing subsequent inversion of configuration in this position from D-gluco to L-ido by an oxidation/reduction sequence.Only 0.08percent of 13 are found in the equilibrium mixture of idose in acidic medium.It is shown with 4-C-methyltalose as example, that the amount of 1,6-anhydrofuranoses in these equilibria rises significantly by changing the hydroxy groups in 4-position from secondary to tertiary ones.