155793-68-3

Upstream product

• 155681-03-1 benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 
• 155793-63-8 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-tert-butoxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 155793-65-0 Trifluoro-methanesulfonic acid (3aR,4R,6S,7R,7aR)-6-tert-butoxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester 
• 190438-46-1 2-((4aR,6S,7R,8R,8aR)-6-tert-Butoxy-8-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 
• 155793-66-1 2-((3aR,4S,6S,7R,7aR)-6-tert-Butoxy-4-iodomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-isoindole-1,3-dione 
• 155793-64-9 2-((3aR,4R,6S,7R,7aR)-6-tert-Butoxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-isoindole-1,3-dione 
• 190438-45-0 2-((2S,3R,4R,5R,6R)-2-tert-Butoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 
• 131234-07-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-α,β-D-galactopyranose 
• 110455-06-6 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α,β-D-galactopyranosyl bromide 

Relevant academic research and scientific papers

Stereoselective syntheses of the O,N-protected subunits of the tunicamycins

The synthesis of the title compounds is described, i.e. coupling of the ylide, generated from the iodophosphonium salt of protected N-phthaloyl-D-galactosamine with 2,3-O-isopropylidene D-ribo-aldehyde afforded an undecose in high yield. Hydroboration-oxidation reaction of the olefinic linkage in the undecose led to the desired tunicamine, as the predominant product. After conversion of the latter to a glycosyl acceptor, this was assembled with the fully protected 2-oxyimino-2-deoxy-α-D-arabino-hexopyranosyl bromide, leading to a trehalose-type α,β-disaccharide.