205934-52-7

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 69940-04-1 (R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol 

Downstream Products

• 205934-53-8 (3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 

Relevant academic research and scientific papers

Studies on the synthesis of the C-glycosidic part of nogalamycin, part 2

The stereochemistry of the addition of metalloaryls 11w-z to the methyl ketones 10a-e was studied in connection with the construction of the nogalamycin C-glycoside. Excellent selectivities towards the (S)-isomer 13a were observed in the β-chelate model B in the reaction of the benzyl ethers 10a with the cerium reagent 11y and the titanium reagent 11z or the alcohol 10c with the lithium compound 11w. A moderate 3:1 selectivity in favor of the desired (R)-isomer was observed in the reaction of the silyl ether 10d with 11w. A reversal of the addition sequence (reaction of 15a with MeMgI) led exclusively to 13a whereas the alcohol 15c gave a 5:3 mixture of 12c:13c.