302593-22-2Relevant academic research and scientific papers
A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline 1,4-Dideoxy-1,4-imino-L-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-L-iditol
Lee, Byong Won,Jeong, Ill-Yun,Yang, Min Suk,Choi, Sang Uk,Park, Ki Hun
, p. 1305 - 1309 (2007/10/03)
The syntheses of pyrrolidine alkaloids (-)-1 and (+)-3 were accomplished in 47 percent and 60 percent overall yield from 2-azido-2-deoxy-L-idonate 5, while piperidine alkaloids (-)-2 and (+)-4 were obtained in 51 percent and 53 percent overall yield from the same starting material. Key step includes iodine promoted one-pot cyclization, and selective deprotection of isopropylidene and 9-phenylfluoren-9-yl (Pf) group.
THE SYNTHESIS OF POLYHYDROXYLATED AMINO ACIDS FROM GLUCURONOLACTONE: ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
Bashyal, Bharat P.,Chow, Hak-Fun,Fellows, Linda E.,Fleet, George W. J.
, p. 415 - 422 (2007/10/02)
The potential of D-glucuronolactone for the synthesis of polyhydroxylated amino acids is illustrated by the enantiospecific syntheses of 2S,3R,4R,5S-trihydroxypipecolic acid, 2R,3R,4R,5S-trihydroxypipecolic acid and 2R,3R,4R-dihydroxyproline.
Synthesis of Two Naturally Occuring Diastereomeric Dihydroxyprolines: 2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline and 2,3-cis-3,4-trans-3,4-Dihydroxy-L-proline
Kahl, Jens-Uwe,Wieland, Theodor
, p. 1445 - 1450 (2007/10/02)
Starting from 2-pyrrolecarboxylic acid the N-Boc derivative 6 is resolved into its optically active constituents by crystalisation with R(+)-1-(4-nitrophenyl)ethaneamin.The N-tosyl-3,4-dehydro-L-proline methyl ester (L-7) derived from this is converted by
