131319-74-9Relevant academic research and scientific papers
Crude D-(+)-Glyceraldehyde Obtained from D-Mannitol-Diacetonide by Oxidative Cleavage with Sodium Periodate: Its Reactions with Nucleophilic Species
Domingos, Jorge L. De O.,Vilela, Guilherme V. M. De A.,Costa, Paulo R. R.,Dias, Ayres G.
, p. 589 - 598 (2004)
The oxidative cleavage of D-(+)-mannitol-diacetonide with sodium periodate lead to a mixture of D-(+)-glyceraldehyde, its hydrate and oligomeric derivatives. In spite of the low concentration of free glyceraldehyde (estimated in ～20%, by NMR), good yields were obtained in nucleophilic additions involving this mixture and a variety of nucleophiles (amines, phosphonates, phosphoranes, nitronates, organometallic compounds).
Asymmetric synthesis of 3,4-disubstituted 2-(trifluoromethyl)pyrrolidines through rearrangement of chiral 2-(2,2,2-trifluoro-1-hydroxyethyl)azetidines
Dolfen, Jeroen,Boydas, Esma Birsen,Van Speybroeck, Veronique,Catak, Saron,Van Hecke, Kristof,D'Hooghe, Matthias
, p. 10092 - 10109 (2017)
Enantiopure 4-formyl-β-lactams were deployed as synthons for the diastereoselective formation of chiral 2-(2,2,2-trifluoro-1-hydroxyethyl)azetidines via trifluoromethylation through aldehyde modification followed by reductive removal of the β-lactam carbonyl moiety. Subsequent treatment of the (in situ) activated 2-trifluoroethylated azetidines with a variety of nitrogen, oxygen, sulfur, and fluorine nucleophiles afforded chiral 3,4-disubstituted 2-(trifluoromethyl)pyrrolidines in good to excellent yields (45-99%) and high diastereoselectivities (dr >99/1, 1H NMR) via interception of bicyclic aziridinium intermediates. Furthermore, representative pyrrolidines were N,O-debenzylated in a selective way and used for further synthetic elaboration to produce, for example, a CF3-substituted 2-oxa-4,7-diazabicyclo[3.3.0]octan-3-one system.
N,Se-Acetals: Preparation and Use in Diastereoselective Radical Reactions
Stojanovic, Aleksandar,Renaud, Philippe
, p. 353 - 373 (2007/10/03)
A new facile synthesis of N,S- and N,Se-acetals starting from aldehydes and primary amines is presented (Schemes 3-5). These acetals are used as precursors for stereoselective radical deuteration and allylation reactions (Schemes 6 and 7, Tables 1 and 2). The stereochemical outcome of the reactions depends on the radical trap and the substituents at the N-atom. Deuterations give always anti products with moderate to high selectivities. The allylation reactions give either syn or anti products with low to moderate selectivities. The observed stereoselectivities can be explained with a model based on minimization of A1,3 strain and are controlled by steric and stereoelectronic effects.
Practical synthesis of α-amino acid N-carboxy anhydrides of polyhydroxylated α-amino acids from β-lactam frameworks. Model studies toward the synthesis of directly linked peptidyl nucleoside antibiotics
Palomo,Oiarbide,Esnal,Landa,Miranda,Linden
, p. 5838 - 5846 (2007/10/03)
A straightforward method for the synthesis of polyhydroxylated α-amino acid N-carboxy anhydrides (NCAs) is described as the means by which short peptide segments comprised of a polyhydroxylated chain are easily affordable. The entire sequence lies in the
A straightforward synthesis of L-isoserinal
Junquera, Federico,Merchan, Francisco L.,Merino, Pedro,Tejero, Tomas
, p. 7045 - 7052 (2007/10/03)
A convenient preparation of L-isoserinal 3 in six steps and 32.8% overall yield employing D-glyceraldehyde acetonide I as starting material is described. The procedure is inexpensive, easily scaled up and proceeds without observable racemization.
N,Se-acetals: Easy preparation and application to radical mediated EPC synthesis
Stojanovic, Aleksandar,Renaud, Philippe
, p. 9199 - 9202 (2007/10/03)
A facile synthesis of N,S- and N,Se-acetals starting from aldehydes and primary amines is presented. These acetals are used as precursors for radical reactions. The stereoselectivity of the reactions depends on the radical trap used.
Total synthesis of 1,5-dideoxy-1,5-iminoalditols
Rassu, Gloria,Pinna, Luigi,Spanu, Pietro,Culeddu, Nicola,Casiraghi, Giovanni,Fava, Giovanna Gasparri,Ferrari, Marisa Belicchi,Pelosi, Giorgio
, p. 727 - 742 (2007/10/02)
Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti, cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.
The Addition of γ-(Trimethylsilyl)allylboronates to Imines
Wuts, Peter G. M.,Jung, Yong-Woon
, p. 365 - 372 (2007/10/02)
The addition of γ-(trimethylsilyl)allylboronates to imines is described and compared with the addition of simple allylboronates to imines.The addition of γ-(trimethylsilyl)allylboronates is found to be more efficient than the addition of simple allylboronates to imines.The stereoselectivity is dependant upon the nature of the imine; imines derived from aromatic aldehydes give anti products and imines derived from aliphatic aldehydes give syn products.Proof of stereochemistry was established by conversion of the anti and syn derivatives to their respective Z- and E-dienes by a methylation/E-2 elimination process.With α-alkoxy aldehydes the reaction proceeds with excellent selectivity giving the product of Felkin-Ahn addition.
