1403588-87-3

Upstream product

• 1403614-60-7 1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(2S)-azido-3-propanol 
• 67-56-1 methanol 
• 1403588-82-8 1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(2R)-ol-3-tert-butyldiphenylsilyloxypropane 
• 1403588-86-2 1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(2S)-azido-3-tert-butyldiphenylsilyloxypropane 
• 179090-11-0 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one 

Downstream Products

• 1403588-88-4 methyl 3C-β-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-L-alanine 

Relevant academic research and scientific papers

Synthesis of β-C-Glycosyl Amino Acids by Ring Opening of Donor-Acceptor Spiro-cyclopropanecarboxylated Sugars

The electrophilic ring opening of donor-acceptor spiro-cyclopropanecarboxylated sugars are shown to provide easy access to the stereoselective synthesis of β-C-glycosyl D- and L-alanine derivatives. A possible mechanism is proposed for the ring-opening reaction based on the obtained crystal structure of one of the spiro-cyclic sugar moieties.

Synthesis of β-C-galactosyl d- and l-alanines

Synthesis of β-C-d-galactosyl d- and l-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and SN2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.