23161-63-9Relevant academic research and scientific papers
Stereoselective synthesis of 3,4-dihydroxylated prolines and prolinols starting from L -tartaric acid
Oba,Koguchi,Nishiyama
, p. 237 - 243 (2014/02/14)
A straightforward and stereoselective synthesis of 3,4-dihydroxyprolines and 3,4-dihydroxyprolinols is described. The key reaction in this synthesis is a protective group-controlled diastereoselective cyanation of a chiral acyliminium intermediate derived from l-tartaric acid. Methanolysis of the obtained cyanolactam gave methyl 3,4-dihydroxypyroglutamate that was converted to 3,4-dihydroxyproline and 3,4-dihydroxyprolinol by reduction of the lactam carbonyl and ester groups in a stepwise manner.
The conversion of pentoses to 3,4-dihydroxyprolines
Taylor, Carol M.,Jones, Chantelle E.,Bopp, Kristin
, p. 9611 - 9617 (2007/10/03)
The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproline was synthesized from L-arabinose in 10 steps and 31% overall yield. The same series of reactions was employed to convert L-xylos
Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)
Garcia, Ariel Lázaro L.,Correia, Carlos Roque D.
, p. 1553 - 1557 (2007/10/03)
cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbamates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent α- and β-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield.
Toward a general strategy for the synthesis of 3,4-dihydroxyprolines from pentose sugars
Taylor, Carol M.,Taylor, Carol M.,Barker, William D.,Weir, Claudette A.,Park, Jae H.
, p. 4466 - 4474 (2007/10/03)
A general strategy is proposed, wherein a pentose sugar γ-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-D-2,3-cis-3, 4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-cis-3, 4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl- 3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.
Efficient synthesis of a new aminoazasugar and dihydroxyprolines from an endocyclic enecarbamate
Pohlit, Adrian M.,Correia, Carlos Roque D.
, p. 2321 - 2325 (2007/10/03)
A novel procedure for the synthesis of trans-2,3-(2-aminomethyl)-cis-3,4-dihydroxypyrrolidine (a new aminoazasugar) and cis-2,3- and trans-2,3-cis-3,4-dihydroxyprolines is presented. Starting from the known endocyclic enecarbamate 1-carbobenzyloxy-2-pyrro
(±)-4-amino-4,5-dideoxyribose, (±)-4-amino-4-deoxyerythrose, and (±)-dihydroxyproline derivatives from N-dienyl-γ-lactams
Behr,Defoin,Mahmood,Streith
, p. 1166 - 1177 (2007/10/02)
Hetero-Diels-Alder cycloaddition of acylnitroso dienophile 4 with the N-(butadienyl)pyrrolidinone derivatives 2a,b led with complete regioselectivity to the oxazine adducts 5a,b. Sequential osmylation, protection of the ensuing glycol, and reduction of th
DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES FOR THE SYNTHESIS OF POLYHYDROXYPYRROLIDINES AS POTENTIAL ENZYMATIC INHIBITORS
Hassan, Mohamed E.
, p. 7 - 9 (2007/10/02)
Tosyl and benzyl azomethine ylides generated from the corresponding aziridines under thermal and photochemical conditions, were trapped by dipolar cycloaddition reaction with vinylene carbonate.The methoxycarbonyl group in the pyrrolidines obtained was re
Synthesis of (3S,4S)-3,4-dihydroxyprolines from L-tartaric acid
Arakawa,Yoshifuji
, p. 2219 - 2224 (2007/10/02)
Natural (2S,3S,4S)-3,4-dihydroxyproline (1) and the new (2R,3S,4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.
EFFICIENT SYNTHESES OF NATURALLY OCCURRING 3,4-DIHYDROXYPROLINES: ELECTROPHILE-MEDIATED LACTONIZATION OF 2-AMINO-3-HYDROXY-4-PENTENOIC ACID DERIVATIVES
Ohfune, Yasufumi,Kurokawa, Natsuko
, p. 5307 - 5308 (2007/10/02)
Stereospecific conversion of β-hydroxyallylglycine derivatives into (2S,3R,4R)1 and (2S,3S,4S)2 via halo- or mercuri-lactonization has been described.
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
