82087-41-0

Upstream product

• 65923-96-8 4,5-Dimethyl-1,2,3-thiadiazol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 38401-84-2 (2S,5R,S)-Chalcogran 
• 82087-42-1 Aldehydo-4-O-benzoyl-2,3,5,6-tetradesoxy-L-glycero-hexose-trimethylendithioacetal 
• 38401-84-2 (2R)-2-Aethyl-1,6-dioxaspiro<4.4>-nonan 

Relevant academic research and scientific papers

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.