870465-58-0

Upstream product

• 247107-78-4 (E)-(C₄H₄NH(CH₂CH₃)(O)(CH₃))C₅H₄O(CH₃)(OH)(CH₃)(CH₂CH(OH)CH(CH₃)CH₂CH₂CHCHSn(n-butyl)3) 
• 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 
• 275805-20-4 (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-7-triethylsilanyl-hept-2-en-6-ynoic acid ethyl ester 
• 275805-22-6 (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-7-triethylsilanyl-hept-2-en-6-yn-1-ol 
• 275805-18-0 (3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-triethylsilanyl-hex-1-en-5-yne 
• 275805-19-1 (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-triethylsilanyl-pent-4-ynal 
• 275805-17-9 (3R,4R)-4-Methyl-1-triethylsilanyl-hex-5-en-1-yn-3-ol 
• 247107-71-7 (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-(S)-4-iodo-1-((E)-2-iodo-1-methyl-vinyl)-but-3-enyl ester 
• 247107-73-9 (S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-(S)-4-iodo-1-((E)-2-iodo-1-methyl-vinyl)-but-3-enyl ester 
• 247107-69-3 (S)-Tetrahydro-pyridazine-1,2,3-tricarboxylic acid 1,2-di-tert-butyl ester 3-[(E)-(S)-4-iodo-1-((E)-2-iodo-1-methyl-vinyl)-but-3-enyl] ester 
• 247107-70-6 (S)-Hexahydro-pyridazine-3-carboxylic acid (E)-(S)-4-iodo-1-((E)-2-iodo-1-methyl-vinyl)-but-3-enyl ester 
• 247107-67-1 tert-Butyl-[(E)-(S)-4-iodo-1-((E)-2-iodo-1-methyl-vinyl)-but-3-enyloxy]-dimethyl-silane 
• 247107-68-2 (1E,5E)-(S)-1,6-Diiodo-2-methyl-hexa-1,5-dien-3-ol 

Downstream Products

• 256424-82-5 26(S),27(S)-dihydroxysanglifehrin A 
• 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 
• 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 
• 870465-61-5 C₆₄H₉₀Cl₃N₅O₁₄ 
• 870465-63-7 C₆₄H₈₈Cl₃N₅O₁₄ 
• 870465-62-6 C₆₄H₉₁N₅O₁₄ 
• 870465-66-0 C₆₂H₈₉N₅O₁₃ 
• 870465-60-4 C₆₄H₉₃N₅O₁₄ 
• 870465-59-1 C₆₂H₉₁N₅O₁₃ 
• 187148-13-6 (-)-sanglifehrin A 

Relevant academic research and scientific papers

Efficient synthesis of [3H]-sanglifehrin A via selective oxidation/reduction of alcohols at C31 and C35

Sanglifehrin A is a novel complex natural product showing strong immunosuppressive activity and remarkably high affinity for cyclophilin A. To assess its pharmacokinetic properties in vivo, an efficient synthetic route was developed to introduce a tritium

Total synthesis of the novel immunosuppressant sanglifehrin A

The total synthesis of the novel immunosuppressant sanglifehrin A (SFA, 1) is described. The approach is flexible, convergent, and stereoselective. The use of Paterson's aldol methodology was pivotal for the preparation of the novel, highly substituted sp

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.