1379680-85-9

Upstream product

• 205934-53-8 (3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 
• 69940-02-9 3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 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 
• 1379680-87-1 (3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-ol 
• 1379680-91-7 (3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yl (3R)-3-(tert-butyldimethylsilyloxy)butanoate 
• 1379680-89-3 (2S,3R)-2-(4-methoxybenzyloxy)pent-4-ene-1,3-diol 
• 1379680-88-2 (3R,4R)-4-(4-methoxybenzyloxy)-5-oxopent-1-en-3-yl formate 

Downstream Products

• 1379680-83-7 (2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate 

Relevant academic research and scientific papers

Total synthesis of macrosphelide M from diacetone glucose

The total synthesis of macrosphelide M is described. The key steps include the preparation of the acid and alcohol fragments from diacetone glucose and (S)-malic acid, respectively, followed by Yamaguchi esterification and macrocyclization of the tris-olefin by ring-closing metathesis. Finally, one-pot deprotection of the PMB and TBS groups with TiCl4 results in the target. The C-3/C-4 stereocenters of diacetone glucose are used for the introduction of four stereocenters, whereas the fifth stereocenter is realized from (S)-malic acid. The total synthesis of macrosphelide M was achieved from diacetone glucose and (S)-malic acid. The key steps include Yamaguchi esterification and macrocyclization of the tris-olefin by the second-generation Grubbs catalyst.