139893-80-4

Upstream product

• 139748-03-1 (S)-4-<(R)-3-benzyloxy-2-(iodomethyl)propyl>-2-azetidinone 
• 139748-08-6 (S)-4-<(SR)-3-benzyloxy-2-(hydroxymethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone 
• 139748-01-9 (S)-4-<(R)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone 
• 139747-96-9 (3S,4S)-4-<(S)-3-benzyloxy-2-(hydroxymethyl)propyl>-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone 
• 139747-98-1 (3S,4S)-4-<(R)-2-benzyloxymethyl-3-(p-toluenesulfonyloxy)propyl>-1-tert-butyldimethylsilyl-3-formylamino-2-azetidinone 
• 139894-73-8 (3S,4S)-4-<(R)-2-benzyloxymethyl-3-(p-toluenesulfonyloxy)propyl>-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone 
• 100-51-6 benzyl alcohol 
• 139747-99-2 (S)-4-<(R)-2-benzyloxymethyl-3-(p-toluenesulfonyloxy)propyl>-1-tert-butyldimethylsilyl-2-azetidinone 
• 139747-95-8 (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone 
• 139747-94-7 (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-3-phthalimido-2-azetidinone 
• 139748-06-4 (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butylidmethylsilyl-3-formylamino-2-azetidinone 
• 139748-07-5 (S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-2-azetidinone 
• 139747-92-5 (2-benzyloxymethyl-2-propenyl)trimethylsilane 
• 113964-32-2 1-{[2-((chloromethyl)allyl)oxy]methyl}-4-methoxybenzene 

Relevant academic research and scientific papers

β-Lactam antifungals. II. Enantiocontrolled synthesis of (2R,5S)-2-hydroxymethyl-1-carbapenam, the carba-analog of a clavam antifungal

(2R,5S)-2-Hydroxymethyl-1-carbapenam (3), the carba-analog of an antifungal β-lactam (2R,5S)-2-(hydroxymethyl)clavam (1), was synthesized in an enantiocontrolled manner, starting from the coupling reaction of an optically active phthalimido-acetate (3S,4S)-4 and an allylsilane 7, followed by removal of the phthalimido group that was crucial for asymmetric induction. Hydroboration, protecting-group interconversion, and cyclization gave 3 stereoselectively.