676265-76-2

Upstream product

• 129706-93-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 158991-97-0 Methyl 3,6-di-O-benzyl-β-D-glucopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 58341-68-7 methyl 3,6-di-O-benzyl-α-D-glucopyranoside 
• 676265-74-0 2,5-anhydro-3,6-di-O-benzyl-4-deoxy-1,4-difluoro-1-O-methyl-D-talitol 

Relevant academic research and scientific papers

A novel approach to the synthesis of N-substituted 1-C-aminomethyl glycofuranosides

Reductive amination of formyl C-glycofuranosides, easily available from hexose-derived equatorial-2-OH-glycopyranosides by DAST-promoted ring contraction, afforded N-substituted 1-C-aminomethyl glycofuranosides in most cases in high yields. Georg Thieme Verlag Stuttgart.

Fluorination of 2-hydroxy-hexopyranosides by DAST: Towards formyl C-glycofuranosides from equatorial-2-OH methyl hexopyranosides

Reaction of diversely configured and substituted, unbranched methyl D-hexopyranosides with the DAST in dichloromethane or acetonitrile led to normal substitution products and/or rearranged fluoro compounds (ring-contracted 2,5-anhydro-1-fluoro-1-O-methylhexitol derivatives, 2-methoxy-D-hexopyranosyl fluorides, and, for some 3-azido substrates, rearranged 2-azido-3-fluoro-D-hexopyranosides). When the reaction was performed in acetonitrile, the solvent participation as a nucleophile (Ritter reaction) was observed in one case. For a 2,4-unprotected 3-azido substrate, 2,3-dehydration and fluorination at C(4), the latter with epimerization, took place. 19F/1H and 19F/13C coupling constant values were systematically applied to discriminate between isomeric structures for fluorinated products, and for some, previously described, coming from five 3-branched-chain D- or L-hexopyranosides, thus discarding the previously reported structural assignment. From the synthetic point of view, the most outstanding result was the preparation of 2,5-anhydro-1-fluoro-1-O- methylhexitols, showing a latent formyl group functionality, a transformation, which was achieved in one case. A rationalization for the formation of the different types of product is also proposed.