- Synthesis of multifunctional 4-hydroxymethyl 2-oxazolidinones from glycidyl carbamate derivatives catalyzed by bicyclic guanidine
-
4-Hydroxymethyl 2-oxazolidinones have been successfully synthesized under mild conditions by the intramolecular cyclization of glycidyl carbamate derivatives with a bicyclic guanidine as the efficient catalyst. This reaction system, which is also applicab
- Yoshida, Yoshiaki,Endo, Takeshi
-
supporting information
(2021/05/03)
-
- Library of 1,4-disubstituted 1,2,3-triazole analogs of oxazolidinone RNA-binding agents
-
The design and synthesis of small molecules that target RNA is immensely important in antibacterial therapy. We had previously reported on the RNA binding of a series of 4,5-disubstituted 2-oxazolidinones that bind to a highly conserved bulge region of bacterial RNA. This biological target T box antitermination system, which is found mainly in Gram-positive bacteria, regulates the expression of several amino acid related genes. In an effort to amplify our library, we have prepared a library of 1,4-disubstituted 1,2,3-triazole analogs that entails an isosteric replacement of the oxazolidinone nucleus. The synthesis of the new analogs was enhanced via copper(I) catalysis of an azide and alkyne cycloaddition reaction. A total of 108 1,4-disubstituted 1,2,3-triazole compounds have been prepared. All compounds were evaluated as RNA binding agents.
- Acquaah-Harrison, George,Zhou, Shu,Hines, Jennifer V.,Bergmeier, Stephen C.
-
scheme or table
p. 491 - 496
(2010/09/15)
-
- Tosylated glycerol carbonate, a versatile bis-electrophile to access new functionalized glycidol derivatives
-
The reactivity of tosylated glycerol carbonate 2 toward nucleophiles has been exploited to generate glycidol analogues protected with carbonate or carbamate groups. The activated glycerol 2 is a reasonable linking agent with thiol and alcohol nucleophiles
- Rousseau, Jolanta,Rousseau, Cyril,Lynikaite, Benita,?a?kus, Algirdas,de Leon, Claudia,Rollin, Patrick,Tatibou?t, Arnaud
-
experimental part
p. 8571 - 8581
(2009/12/24)
-
- Rearrangements and racemisation during the synthesis of L-serine derived oxazolidin-2-ones
-
The propensity for N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O carbonyl transfer makes these L-serine derived chiral auxiliaries unsuitable for attachment to polymers.
- Bew, Sean P,Bull, Steven D,Davies, Stephen G,Savory, Edward D,Watkin, David J
-
p. 9387 - 9401
(2007/10/03)
-
- Polymer supported oxazolidin-2-ones derived from L-serine - A cautionary tale
-
The capacity of N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O acyl transfer makes these serine derived chiral auxiliaries unsuitable for attachment to polymers. (C) 2000 Elsevier Science Ltd.
- Bew,Bull,Davies
-
p. 7577 - 7581
(2007/10/03)
-
- Nucleophilic ring opening of cyclic sulphamidites
-
The cyclic sulphamidities (2S,4S)- and (2R,4S)-3-benzyl-4-benzyloxymethyl-2-oxo-1,2,3-oxathiazolidine 1 were prepared from S-glycidol in 60-66% overall yield. Nucleophilic ring opening of 1 by cyanide, azide and benzyloxy anions have been studied with respect to regio and stereospecificity. A mild procedure for benzylation of alcohols was introduced.
- Gautun,Carlsen
-
p. 1667 - 1674
(2007/10/02)
-