New Synthesis of Chiral 1,3-Oxazinan-2-ones from Carbohydrate Derivatives

Ella‐Menye, Jean‐Rene; Sharma, Vibha; Wang, Guijun

doi:10.1021/jo040224q

Cited by 35 publications

(24 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The weak triplet at 1.13 ppm corresponded with 1 "H. As in PTOBDME-choline, the choline end group shows, inTable 2, two set of signals due to conformational equilibrium. Multiplets 13 H,14 H are observed at 4.56 and 3.32 ppm, respectively, and 15 H at 2.74 ppm, correlated in COSY experiments, and another set was13 'H and 14 'H multiplets at 4.75 and 3.84 ppm, respectively, singlet15 'H at 3.22 ppm.…”

mentioning

confidence: 80%

“…Poly[oxy(1,2-undecan-11-amidyl)-oxycarbonyl-1,4-phenylene-oxy-1,4-terephthaloyl-oxy-1,4-phenylene-carbonyl], VII in Figure 4, was obtained through polycondensation reaction between 4 and 4′-(terephthaloyldioxydibenzoic chloride) TOBC and the racemic mixture of DL-10,11-dihydroxyundecanemide (V in Figure 4) [11][12][13][14][15]. Similar notation has been used than with precursor cholesteric liquid crystal PTOBDME, Figure 1.…”

Section: Synthesis Of Cholesteric Ptobume-amide [(C 33 H 33 O 9 N) Nmentioning

confidence: 99%

See 1 more Smart Citation

Synthetic Cationic Cholesteric Liquid Crystal Polymers

Méndez¹

2018

Liquid Crystals - Recent Advancements in Fundamental and Device Technologies

View full text Add to dashboard Cite

We report the synthesis of six multifunctional cationic cholesteric liquid crystals polyesters functionalized with choline, amine, and amide groups to obtain new chemical formulations involving macromolecular features with new properties added to those of precursor chiral cholesteric polyesters. They are designed as PTOBDME-choline [(C 34 H 36 O 8) n ─C 5 H 13 N]; PTOBEE-choline [(C 26 H 20 O 8) n ─C 5 H 13 N]; PTOBDME-ammonium [(C 34 H 36 O 8) n ─C 5 H 13 N]; PTOBEE-ammonium [(C 26 H 20 O 8) n ─C 5 H 13 N]; PTOBUME-amide (C 33 H 33 O 9 N) n ; and PTOBEE-amide (C 26 H 19 O 9 N) n. Structural characterization is performed by NMR. Thermal behavior is studied by thermogravimetry (TG) and differential scanning calorimetry (DSC), showing all the polymers endothermic transition from crystal phase to liquid crystal mesophase. Chirality is determined by optical rotatory dispersion (ORD). The cationic cholesteric liquid crystal polymers described here have proved to act as nonviral vectors in gene therapy, transfecting DNA to the nucleus cell.

show abstract

mentioning

confidence: 80%

Section: Synthesis Of Cholesteric Ptobume-amide [(C 33 H 33 O 9 N) Nmentioning

confidence: 99%

Synthetic Cationic Cholesteric Liquid Crystal Polymers

Méndez¹

2018

Liquid Crystals - Recent Advancements in Fundamental and Device Technologies

View full text Add to dashboard Cite

show abstract

“…Prior to examination of the reactions and release of label from the propylamine functionalized SiNPs, free propylamine was used as a model compound for the NPs. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Propylamine was reacted with -hydroxy--butyrolactone (Scheme 2) (a modification of the literature procedure 28 ) to generate an amide with a 1,2-diol structure (Scheme 2; 5). The reaction using neat reagents proceeded quantitatively.…”

Section: Synthesis Of the Mass Label (Scheme 1; 2) And The Model Diolmentioning

confidence: 99%

Molecular labels for analysis of amines and diols by spray based ionization-mass spectrometry

Ayrton

Cooks

Pugia

2016

Analyst

View full text Add to dashboard Cite

A family of imidazolium and pyridinium salts was synthesized for the purpose of labeling amines and 1,2-diols for highly sensitivite analysis by mass spectrometry. The chosen mass labels are shown to serve as effective reporters when bound to particles functionalized with amines or 1,2-diols and the binding is reversible. The straightforward synthetic route allows analogous internal standards to be generated quickly. Solvents amenable to electrospray ionization facilitate the rapid liberation of imidazolium and pyridinium mass labels from particles by hydrolysis in aqueous acid, while the acetal bond remains stable in anhydrous or buffered aqueous solution. Detection of the labels is demonstrated at 1 nM and quantitation of mass labels released from particles is also demonstrated.

show abstract

“…Scheme 1: Synthetic approaches to 1,3-oxazinan-2-ones [38][39][40][41][42][43][44][45][46][47][48][49][50].…”

Section: Introductionmentioning

confidence: 99%

1,3-Oxazinan-2-ones via carbonate chemistry: a facile, high yielding synthetic approach

Aricò

Bravo

Crisma

et al. 2016

Pure and Applied Chemistry

View full text Add to dashboard Cite

A high yielding synthesis of 1,3-oxazinan-2-ones starting from 3-amino-1-propanols and ethylene\ud carbonate (EC) in the presence of catalytic amount of triazabicyclodecene (TBD) is herein reported. The formation\ud of six-membered cyclic carbonates was achieved by intermolecular cyclization reaction via double\ud BAc2 mechanism. Cyclization reactions have been carried out in neat as EC acted both as solvent and reagent.\ud Pure 1,3-oxazinan-2-ones were isolated in high yield by simple liquid-liquid extraction. Further purification\ud can be achieved by recrystallization. The reaction resulted of general application on different substrates\ud including an aryl bis(3-amino-proan-1-ol) compound

show abstract

New Synthesis of Chiral 1,3-Oxazinan-2-ones from Carbohydrate Derivatives

Cited by 35 publications

References 27 publications

Synthetic Cationic Cholesteric Liquid Crystal Polymers

Synthetic Cationic Cholesteric Liquid Crystal Polymers

Molecular labels for analysis of amines and diols by spray based ionization-mass spectrometry

1,3-Oxazinan-2-ones via carbonate chemistry: a facile, high yielding synthetic approach

Contact Info

Product

Resources

About