113299-34-6Relevant academic research and scientific papers
AN ALTERNATIVE SYNTHESIS OF (1R,2S,3R,4R)-2,3-DIHYDROXY-4-HYDROXYMETHYL-1-CYCLOPENTANAMINE, A SYNTHETIC INTERMEDIATE OF (-)-ARISTEROMYCIN
Tadano, Kin-ichi,Hoshino, Masahide,Ogawa, Seiichiro,Suami, Tetsuo
, p. 2741 - 2744 (1987)
The title compound, an enantiomerically pure carbocyclic portion of the antibiotic (-)-aristeromycin, has been synthesized from D-erythrose.The synthesis involves a transformation of the known carbocyclic analogue of β-L-arabinofuranose to the α-D-ribo fo
Transformation of D-Erythrose to Some Pseudoaldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and (1R,2S,3S,4S)-2,3,4-Trihyroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-Dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine
Tadano, Kin-ichi,Hoshino, Masahide,Ogawa, Seiichiro,Suami, Tetsuo
, p. 1427 - 1432 (2007/10/02)
Sodium borohydride reduction of (1S,3S,4S)-1--3,4-(isopropylidenedioxy)-2-cyclopentanone (11), which was prepared from D-erythrose, proceeds exlusively from the β-face to provide 2R-hydroxyl derivative 12.Compound 12 is a derivative of carbocyclic analogue of β-L-lyxofuranose.Silica gel promoted configurational inversion at the branched carbon in 11 followed by sodium borohydride reduction provides 1R,2R diastereomer 17 and 12 a 2.8:1 ratio.The former is a protected form of carboxylic α-D-ribofuranose.Replacement of the mesyloxy group in 23, which was derived from 17, by a hydroxyl group in a SN2 fashion and deprotection of the product followed by acetylation gave a derivative of carbocyclic α-D-xylofuranose 24.Compound 17 was also converted to compound 7, a key intermediate for the synthesis of the carboxylic nucleoside antibiotic (-)-aristeromycin (1), via a SN2 replacement of the mesyloxy group in 26 by an azide group.
