869639-06-5

Upstream product

• 146608-95-9 ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 869639-01-0 ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-phenylcarbamoyl-1-thio-β-D-glucopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 869639-07-6 ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside 
• 869639-08-7 ethyl 6-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Convenient construction of a variety of glycosidic linkages using a universal glucosyl donor

This letter deals with the concept of constructing four types (cis-α, trans-α, cis-β, and trans-β) of glycosidic linkages using a universal glucosyl donor. The selectively protected universal glucosyl donor 8 was synthesized in 36% yield from d-glucose (eight steps). The donor 8 undergoes glycosidation with a primary carbohydrate alcohol 7 to give disaccharide 9 having a 1,2-cis-α-glycosidic linkage in 90% yield. The construction of the corresponding 1,2-trans-α-glycosidic linkage was performed in 68% yield (three steps) from 9. A similar glycosidation of the 2-O-(N- phenylcarbamoyl)-glucosyl donor 6 derived from 8 with 7 gave disaccharide 11 having a 1,2-trans-β-glycosidic linkage in 75% yield. The construction of the corresponding 1,2-cis-β-linkage was performed in 53% yield (three steps) from 11.