95069-12-8

Upstream product

• 121846-10-4 1-<(11R)-1,3,4,7,9,10-Hexa-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,6-dideoxy-L-allo-α-D-galacto-undecodialdo-1,5-pyranose-11,8-furanosyl>-3-(4-methoxybenzyl)uracil 
• 108-24-7 acetic anhydride 
• 87256-68-6 1-<(11S)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-11-O-methyl-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil 

Downstream Products

• 95069-14-0 1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-glucopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil 
• 95069-14-0 1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-β-D-glucopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil 
• 95069-15-1 1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-10-(benzyloxycarbonyl)amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil 
• 66054-36-2 tunicamycin V 
• 95069-13-9 1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil 

Relevant academic research and scientific papers

Fully synthetic stereoselective routes to the differentially protected subunits of the tunicamycins

Total synthesis of the two subunits corresponding to tunicamycins have been achieved. One of the key steps involves a cyclocondensation reaction of 7-carbon aldehydo nucleoside with activated diene 8 under catalysis with stannic chloride (see 7 + 8→9a,b). Stereospecific Fitzsimmons cycloadditions of dibenzyl azodicarboxylate to galactal 12 and glucal 22 simplified construction of the amino pyranose systems.

TOTAL SYNTHESIS OF TUNICAMYCIN

The first total synthesis of tunicamycin V, a major component of tunicamycin homologues, is described.Condensation of 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-glucopyranose with 1-(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)ami