11475-55-1

Upstream product

• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 118475-51-7 1,6-Anhydro-2,3-di-O-benzyl-5-O-(trifluormethylsulfonyl)-α-L-idofuranose 
• 81937-01-1 1,6-Anhydro-2,3-di-O-benzyl-α-L-idofuranose 
• 51516-26-8 1,6-Anhydro-2,3-di-O-benzyl-β-D-glucofuranose 
• 81936-96-1 1,6-Anhydro-2,3-di-O-benzyl-β-D-xylo-hexofuranos-5-ulose 
• 108-24-7 acetic anhydride 
• 118475-52-8 1,6-Anhydro-5-azido-2,3-di-O-benzyl-5-desoxy-β-D-glucofuranose 

Relevant academic research and scientific papers

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