256424-82-5

Upstream product

• 870465-58-0 sanglifehrin A ketal 
• 256326-89-3 (2S,3S,4S,5S,6R,9S,11S)-9-Ethyl-3,5,11-trimethyl-2-[(2S,3S)-3-methyl-6-(1-phenyl-1H-tetrazole-5-sulfonyl)-2-triethylsilanyloxy-hexyl]-4-triethylsilanyloxy-1-oxa-7-aza-spiro[5.5]undecan-8-one 
• 256326-88-2 (2S,3S,4S,5S,6R,9S,11S)-9-Ethyl-3,5,11-trimethyl-2-[(2S,3S)-3-methyl-6-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-2-triethylsilanyloxy-hexyl]-4-triethylsilanyloxy-1-oxa-7-aza-spiro[5.5]undecan-8-one 
• 187148-13-6 (-)-sanglifehrin A 

Downstream Products

• 256326-87-1 (2S,3R,4S,5S,6R,9S,11S)-9-Ethyl-4-hydroxy-2-[(2S,3S)-2-hydroxy-3-methyl-6-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-hexyl]-3,5,11-trimethyl-1-oxa-7-aza-spiro[5.5]undecan-8-one 
• 256326-85-9 (2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-2-(((2S,3S)-6-hydroxy-3-methyltetrahydro-2H-pyran-2-yl)methyl)-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one 
• 256424-81-4 (E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal 

Relevant academic research and scientific papers

Toward a Total Synthesis of the Immunosuppressant Sanglifehrin A. Preparation of Two Relay Compounds by Degradation and Their Use in the Reassembly of the Natural Product

A potential relay route for the synthesis of the novel immunosuppressive agent sanglifehrin A (1) has been developed. Degradation of 1 by a sequence involving regioselective dihydroxylation of the C26,C27 double bond, followed by periodate cleavage of the resulting diol 4, afforded lactol 2 and macrocyclic aldehyde 3. Intramolecular ketal formation between the 1,3-diol and ketone functions present in 3 gave ketal-aldehyde 5. Lactol 2 was converted into sulfone 14 in four steps. The fragments 5 and 14 were reassembled, using the Julia-Kocienski olefination procedure, to afford intermediate 15, which was converted back to sanglifehrin A (1) after two deprotection steps.