192753-80-3

Upstream product

• 87-72-9 L-xylopyranose 
• 120522-10-3 2,3,4,5-di-O-isopropylidenealdehydo-L-xylose 
• 192753-59-6 2,3,4,5-di-O-isopropylidene-L-xylose diethyl dithioacetal 
• 192753-67-6 (2S,3R,4S)-2,3,4,5-tetrahydroxy-2,3:4,5-di-O-isopropylidene-1-C-(2-thiazolyl)-1-pentanone 
• 23259-79-2 L-xylose diethyl dithioacetal 
• 609-06-3 L-xylose 
• 100-39-0 benzyl bromide 
• 192753-62-1 1,2,3,4-bis-O-(1-methylethylidene)-5-C-2-thiazolyl-(5S)-D-xylitol 

Downstream Products

• 162111-91-3 3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate 

Relevant academic research and scientific papers

SACCHARIDE CONJUGATES

This invention relates to compounds comprising a saccharide conjugated to an imaging agent or a reporter group, compositions comprising them and methods of using them. Specifically BLM-disaccharide and BLM-monosaccharide conjugates containing different linker groups and an imaging agent or a reporter group are provided for the targeting and imaging of tumors.

Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2

The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.