214596-91-5

Upstream product

• 1194-02-1 4-fluorobenzonitrile 
• 214596-87-9 [2R,3S]-2-amino-4-methyl-1-(tetrahydropyran-2-yloxy)pentan-3-ol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 125414-63-3 4-(4S)-hydroxymethyl-5-(5R)-isopropyloxazolidin-2-one 
• 217495-59-5 [2R]-dibenzylamino-3-(tetrahydropyran-2-yloxy)propionaldehyde 
• 217495-58-4 [2S]-dibenzylamino-3-(tetrahydropyran-2-yloxy)propan-1-ol 
• 217495-60-8 [2R,3S]-2-dibenzylamino-4-methyl-1-(tetrahydropyran-2-yloxy)pentan-3-ol 
• 217495-57-3 [2R]-dibenzylamino-3-(tetrahydropyran-2-yloxy)propionic acid methyl ester 
• 214596-86-8 (4R,5S)-5-Isopropyl-4-(tetrahydro-pyran-2-yloxymethyl)-oxazolidin-2-one 

Downstream Products

• 214596-88-0 [[1R,2S]-2-(4-cyanophenoxy)-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl]carbamic acid tert-butyl ester 
• 214596-89-1 {[1R,2S]-2-[4-(1-hydroxy-2-nitroethyl)phenoxy]-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl}carbamic acid tert-butyl ester 
• 214596-93-7 {[1R,2S]-2-[4-(2-amino-1-hydroxyethyl)-phenoxy]-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl}carbamic acid tert-butyl ester 
• 214596-92-6 [[1R,2S]-2-(4-formylphenoxy)-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl]carbamic acid tert-butyl ester 
• 214596-90-4 ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester 
• 171618-25-0 (2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-acetyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 
• 214900-86-4 (2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-ethyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid pentafluorophenyl ester 
• 214900-85-3 (2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-ethyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 

Relevant academic research and scientific papers

Total synthesis of the cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer

The naturally occurring cyclopeptide alkaloid sanjoinine G1 and its C- 11 epimer were synthesized in 18 steps from D-serine. The key steps in the synthesis were the formation of the alkylaryl ether linkage via an S(N)Ar reaction with 4-fluorobenzonitrile

Synthetic studies of 14-membered cyclopeptide alkaloids

A strained 14-membered cyclopeptide was prepared from the Garner aldehyde derived from D-serine. The key steps in the synthesis were the construction of the alkyl-aryl ether linkage via an S(N)Ar reaction involving 4-fluorobenzonitrile and the macrolactamization using a modification of the Schmidt protocol involving an activated pentafluorophenyl ester.