82087-33-0

Upstream product

• 58475-20-0 3,5-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 74707-99-6 5,6-Di-O-acetyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 58475-16-4 [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxol-5-yl]-2-hydroxy-ethyl]4-methylbenzenesulfonate 
• 316804-22-5 3-deoxy-1,2-O-isopropylidene-5-O-(thiocarbonylimidazolyl)-6-O-tosyl-α-D-ribo-hexofuranose 
• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 

Relevant academic research and scientific papers

Synthesis of kanamycin A analogs containing a 6-amino-6-deoxyglycofuranose moiety

Three kanamycin A analogs containing 6-amino-6-deoxyglycofuranoses have been prepared as candidates for potential activity against resistant bacteria producing 6'-N-acetyltransferase. They are 4-O-(6-amino-3,5,6-trideoxy-α-D-, -β-D-, and -β-L-erythro-hexofuranosyl)-6-O-(3-amino-3-deoxy-α-D-glucopyran osyl)-2,5-dideoxy-5-epi-5-fluorostreptamine. Structure-activity relationships of these compounds are discussed. (C) 2000 Published by Elsevier Science Ltd.

Chiral Building Units from Carbohydrates, VI. - Synthesis of (2R,5RS)- and (2S,5RS)-2-Ethyl-1,6-dioxaspirononane (Chalcogran) from D-Glucose

Starting from D-glucose the syntheses of the title compounds (15 and 25) are described.Key compounds are the tetradeoxytrimethylenedithioacetals 11 and 23 which lead by the Corey-Seebach reaction with the THP-blocked 3-bromo-1-propanol to the fully blocked, open-chained products 13 and to the (S)-analogous compound.Mild cleavage of the dithiane group and the THP-protective groups yields after spontaneous cyclisation 15 and 25.The open-chained mono-ol 11 with D-configurated hydroxyl group can be converted into the L-configurated product 22 by esterification with benzoic acid/ triphenylphosphane/ diethyl azodicarboxylate.