Reaction of 4-methyl-3,4-epoxytetrahydropyran with ?-amino acids

Ibatullin, U. G.; Vasil'eva, S. A.; Karimova, Z. Kh.; Latypova, I. Z.; Safarov, M. G.

doi:10.1007/bf00473859

Cited by 2 publications

(2 citation statements)

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“…20 On the other hand, the presence of protonic solvents such as ethanol, methanol, and water could enhance the reactivity of amino group but not that of hydroxyl group. 13,15,21 In our reaction system, the selected amino acid was derived to alkaline metal carboxylate by the addition of equal mole amount of inorganic alkali such as sodium hydroxide, and then the amino group of amino acid in free form in the alkaline reaction system could initiate the ring opening of ethylene oxide more effectively compared to the usual protonated form in neutral or acidic solution.…”

Section: Resultsmentioning

confidence: 99%

“…However, amino group showed great nucleophilic attack ability in the ring-opening reaction of epoxide compounds. [13][14][15][16][17][18][19][20] Micheloni et al synthesized bis(2-chloroethyl) pentylamine by the nucleophilic attack of pentylamine on ethylene oxide with ethanol as solvent. 14 Chakraborti et al have used montmorillonite K 10 to catalyze the ring opening of epoxides by amines under solvent-free conditions at room temperature and produced 2-amino alcohols.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of heterotelechelic poly(ethylene glycol)s with amino acid at one end and hydroxyl group at another end

Zhang

2008

J of Applied Polymer Sci

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Heterotelechelic poly(ethylene glycol)s are widely used in the modification, conjugation, and crosslinking of biomacromolecules. A series of heterotelechelic PEGs with amino acid at one end and hydroxyl group at another end, including α‐glycine‐ω‐hydroxyl‐PEG, α‐proline‐ω‐hydroxyl‐PEG, and α‐phenylalanine‐ω‐hydroxyl‐PEG, were first synthesized in this study. The reaction proceeded at ambient temperature under alkaline conditions via an aqueous solution polymerization of ethylene oxide. Amino group of glycine, proline, and phenylalanine was the initiating center in the polymerizations, and carboxyl group of these amino acids was reserved as one of the active end groups of the obtained heterotelechelic PEG. Purification of the desired products was accomplished by silica gel column chromatography. The obtained heterotelechelic PEGs were characterized by means of FT‐IR, 1H NMR, 13C NMR, MS, and RP‐HPLC. They were in different forms depending on the type of initiating amino acid, e.g. α‐glycine‐ω‐hydroxyl‐PEG and α‐phenylalanine‐ω‐hydroxyl‐PEG are in branched form, and α‐proline‐ω‐hydroxyl‐PEG is linear. Amino acids were conjugated to PEG chains through the stable carbon–nitrogen bond. Compared with the traditional critical polymerization conditions, the advantage of this method is that various amino acid ended heterotelechelic PEGs can be designed and obtained by using different amino acid as the initiator through a much more convenient route, which proceeded in aqueous solution at ambient temperature. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of heterotelechelic poly(ethylene glycol)s with amino acid at one end and hydroxyl group at another end

Zhang

2008

J of Applied Polymer Sci

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Application of D‐chiro‐Inositol as a Chiral Template for the DielsAlder Reaction

Trant

Belding

Dudding

et al. 2012

Helvetica Chimica Acta

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The DielsAlder reaction can reliably provide the expected endo‐product in the presence of secondary orbital overlap. It can be considerably more difficult to access a single enantiomer of the exo‐product. In this paper, a D‐chiro‐inositol derivative is used as a chiral tether to facilitate the regio‐, diastereo‐, and enatioselective cycloaddition between cinnamic acid and hexa‐3,5‐dienoic acid. The DielsAlder reaction between these two substrates, or their respective esters, does not occur under thermal conditions. Because of the ease of removal of the chiral tether from the resulting cyclohexene, this approach could provide a viable technique to access otherwise unavailable systems.

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Reaction of 4-methyl-3,4-epoxytetrahydropyran with ?-amino acids

Cited by 2 publications

References 1 publication

Synthesis and characterization of heterotelechelic poly(ethylene glycol)s with amino acid at one end and hydroxyl group at another end

Synthesis and characterization of heterotelechelic poly(ethylene glycol)s with amino acid at one end and hydroxyl group at another end

Application of D‐chiro‐Inositol as a Chiral Template for the DielsAlder Reaction

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