56543-10-3Relevant academic research and scientific papers
High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues
Moreaux, Maxime,Bonneau, Guillaume,Peru, Aurélien,Brunissen, Fanny,Janvier, Marine,Haudrechy, Arnaud,Allais, Florent
supporting information, p. 1600 - 1604 (2019/01/14)
A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.
First asymmetric total synthesis of aspergillide D
Jena, Bighnanshu K.,Reddy, G. Sudhakar,Mohapatra, Debendra K.
, p. 1863 - 1871 (2017/03/09)
The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from d-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.
Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: Scope, limitations and stereoselectivity
Stockwell, Jennifer,Daniels, Adam D.,Windle, Claire L.,Harman, Thomas A.,Woodhall, Thomas,Lebl, Tomas,Trinh, Chi H.,Mulholland, Keith,Pearson, Arwen R.,Berry, Alan,Nelson, Adam
supporting information, p. 105 - 112 (2015/12/30)
The catalysis of reactions involving fluoropyruvate as donor by N-acetyl neuraminic acid lyase (NAL) variants was investigated. Under kinetic control, the wild-type enzyme catalysed the reaction between fluoropyruvate and N-acetyl mannosamine to give a 90-10 ratio of the (3R,4R)- and (3S,4R)-configured products; after extended reaction times, equilibration occurred to give a 30-70 mixture of these products. The efficiency and stereoselectivity of reactions of a range of substrates catalysed by the E192N, E192N/T167V/S208V and E192N/T167G NAL variants were also studied. Using fluoropyruvate and (2R,3S)- or (2S,3R)-2,3-dihydroxy-4-oxo-N,N-dipropylbutanamide as substrates, it was possible to obtain three of the four possible diastereomeric products; for each product, the ratio of anomeric and pyranose/furanose forms was determined. The crystal structure of S. aureus NAL in complex with fluoropyruvate was determined, assisting rationalisation of the stereochemical outcome of C-C bond formation.
A heterogeneous Pd-Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars
Fan, Ao,Jaenicke, Stephan,Chuah, Gaik-Khuan
supporting information; experimental part, p. 7720 - 7726 (2011/12/04)
A critical step in the synthesis of the rare sugars, l-lyxose and l-ribose, from the corresponding d-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5:1 atomic ratio of Pd:Bi. The overall yields of the five-step procedure to l-ribose and l-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.
Looking glass inhibitors: Efficient synthesis and biological evaluation of D-deoxyfuconojirimycin
Bleriot, Yves,Gretzke, Dirk,Kruelle, Thomas M.,Butters, Terry D.,Dwek, Raymond A.,Nash, Robert J.,Asano, Naoki,Fleet, George W.J.
, p. 2713 - 2718 (2007/10/03)
1,6-Dideoxygalactostatin, the mirror image of 1-deoxy-L-fuconojirimycin, was efficiently prepared from 2,3-O-isopropylidene-L-lyxonolactone in four steps and evaluated as a glycosidase inhibitor.
Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols
Godskesen, Michael,Lundt, Inge,Sotofte, Inger
, p. 567 - 579 (2007/10/03)
Reaction of 4-O-sulfonylated 2,3-O-isopropylidene-D-ribo- or -D-lyxo-1,5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-lyxo-5 or -L-ribo-15-1,4-lactams, respectively. A stereospecific ring contraction with inversion at C-4 had taken place in each case. Reduction of the cyano-lactams with LiAlH4 gave 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-lyxo-6 or -L-ribo-16-hexitol, respectively. The 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-ribo-hexitol 16 was found to be a moderate inhibitor of α-L-fucosidase with a K(i) of 110 μM. Copyright (C) 2000 Elsevier Science Ltd.
Stereoselective transformations leading to pentono -1, 4-lactones
Rao, B. Venkateswara,Lahiri, Saswata
, p. 975 - 984 (2007/10/03)
The readily available 2, 3-O-isopropylidene-D-erythrose has been stereoselectively transformed into L-ribono and D/L lyxonolactone derivatives via dihydroxylation, iodolactonisation and epoxidation. Also D-ribono-1,4-lactone was converted into L-lyxono-1,
Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones
Han,Joullie,Fokin,Petasis
, p. 2535 - 2562 (2007/10/02)
The different reactivities of D-ribonolactone, L-arabinonolactone, D-xylonolactone, D-lyxonolactone and 2-deoxy-D-ribonolactone toward benzaldehyde and acetone in acidic media, were examined. The reactions involved complex equilibria and were investigated with extensive 13C NMR studies as well as X-ray crystallographic analysis of selected products. Molecular mechanics (MM2) and semiempirical (PM3 and AM1) calculations of some derivatives were carried out in order to facilitate structural and conformational assignments. The differences in reactivity observed for the reactions of D-pentono-1,4-lactones with benzaldehyde and acetone are rationalized in terms of their structural and conformational features.
Synthesis of L-Ribono- and L-Lyxono-lactone
Kold, Henriette,Lundt, Inge,Pedersen, Christian
, p. 675 - 678 (2007/10/02)
L-Ribonolactone has been prepared in good yield by treatment of 2,3-O-isopropylidene-5-O-methanesulfonyl-D-lyxono-1,4-lactone with aqueous base.It was isolated as 3,4-O-benzylidene-L-ribono-1,5-lactone.A similar treatment of 2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactone gave L-lyxonolactone, isolated as the 3,5-O-benzylidene derivative.The mechanisms of the reactions, as well as those of the reaction of 5-bromo-5-deoxy-D-ribono- and -D-lyxono-1,4-lactone, with aqueous base have been studied.
