71461-13-7

Usage

InChI:InChI=1/C28H36N4O4/c33-21-8-5-19(6-9-21)27-26-22-17-20(7-10-24(22)36-27)23-18-25(34)31-14-4-16-32(28(26)35)15-2-1-11-29-12-3-13-30-23/h5-10,17,23,26-27,29-30,33H,1-4,11-16,18H2,(H,31,34)/t23-,26+,27-/m0/s1

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 566203-08-5 O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A 
• 69721-57-9 (11S,17S,18S)-aphelandrine 
• 373360-25-9 (-)-(S)-8-(4-methoxyphenyl)-1,13-bis[(4-methylphenyl)sulfonyl]-1,5,9,13-tetraazacycloheptadecan-6-one 
• 444119-35-1 (-)-(S)-N-(3-aminopropyl)-3-({3-[(4-methylphenylsulfonyl)amino]propyl}amino)-(4-methoxyphenyl)propanamide 
• 360059-20-7 (S)-3-Amino-3-(4-methoxy-phenyl)-propionic acid ethyl ester 
• 321835-85-2 (-)-(S)-3-(4-methoxyphenyl)-N-{3-[(4-methylphenylsulfonyl)amino]propyl}-3-({3-[(4-methylphenylsulfonyl)amino]propyl}amino)propanamide 
• 321835-84-1 (-)-(8S)-1-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 
• 151813-62-6 (-)-(S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 566202-95-7 (2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester 
• 566203-10-9 acetic acid 3-[[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-(2-nitro-benzenesulfonyl)-amino]-propyl ester 
• 795296-97-8 (2R,3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-benzyloxycarbonylamino-2-chloropropionic acid methyl ester 
• 566203-00-7 (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-{benzyloxycarbonyl-[3'-(2''-nitrobenzenesulfonylamino)propyl]amino}propionic acid methyl ester 

Downstream Products

• 71384-31-1 (1S,18²R,18³R)-18²-(3,5-dibromo-4-hydroxy-phenyl)-18^2,3-dihydro-2,6,11,15-tetraaza-18(5,3)-benzofurana-bicyclo[9.6.2]nonadecaphane-16,19-dione 

Relevant academic research and scientific papers

The Absolute Configuration of the Spermine Alkaloid Aphelandrine

The relative configuration of aphelandrine (1) was established by X-ray structure determination.The absolute configuration of the centers 11 and 18 was determined earlier by chiroptic measurements.Therefore, structure 1 with the configurations 11S, 17S, and 18S represents the absolute configuration of aphelandrine.In the presence of base, 1 was converted to (11S, 17R, 18R)-orantine (2).The 1H-NMR coupling constants between H-C(17) and H-C(18) (part of the dihydrofuran ring) are very much dependent on the substituent pattern of the amino N-atoms N(6) and N(10).

Total synthesis of (-)-ephedradine A: An efficient construction of optically active dihydrobenzofuran-ring via C-H insertion reaction

The stereocontrolled total synthesis of (-)-ephedradine A (1) has been accomplished. Construction of optically active dihydrobenzofuran-ring was performed by a novel asymmetric C-H insertion reaction. After an intramolecular ester-amide exchange reaction and a Sharpless asymmetric aminohydroxylation reaction, construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction. Graphical Abstract.

Stereocontrolled total synthesis of (-)-ephedradine a (orantine)

The stereocontrolled total synthesis of (-)-ephedradine A has been accomplished. The synthesis features an asymmetric C-H insertion reaction, an intramolecular ester-amide exchange reaction, and a Sharpless asymmetric aminohydroxylation reaction. Construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction. Copyright

Biomimetic formation of macrocyclic spermine alkaloids

Dihydroxyverbacine (10), a precursor for oxidative phenol coupling, was obtained via (±)-buchnerine (14), whose synthesis is described. The oxidizing system hemin (ferriprotoporphyrin IX chloride)/H2O2 promoted intramolecular coupling of 10 to give the alkaloids aphelandrine (1), orantine (2), and chaenorpine (7). The alkaloids were identified by on-line coupled HPLC and atmospheric-pressure chemical-ionization (APCI) mass spectrometry.