Some derivatives of 6-amino-6-deoxy-d-gluconic acid that are precursors for the synthesis of polyamides

Martı́nez, Manuel Bueno; Mata, Francisca Zamora; Donoso, María Teresa Ugalde; Pérez, Juan Manuel Sánchez

doi:10.1016/s0008-6215(00)90522-6

Cited by 17 publications

(8 citation statements)

References 5 publications

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“…Opening of lactones 10 and 13 with methyl iodide as described previously [5][6][7] was unsuccessful. Under those conditions very complex mixture of products were formed, most of them showing (TLC) intense absorbance under UV light which, together with the NMR data, indicated the presence of conjugated unsaturated systems.…”

Section: Resultsmentioning

confidence: 99%

“…Oxidation of 22 with PCC in dichloromethane yielded lactone 23 (87%). However, treatment of 23 with methyl iodide, under the conditions known [5][6][7] to open the In conclusion, due to the easy elimination of the azido group at C-3 of lactone 13, attempts to open the lactone ring under basic conditions did not give good yields of 16, the precursor of the amino acid 2, but mixtures of ␣,␤-unsaturated carbonyl compounds were obtained instead. However, compound 16 was obtained in low to moderate yield, in two steps, by treatment of 13 with camphorsulfonic acid, then methylation of OH-5 of 14, under mild conditions, with silver oxide and methyl iodide.…”

Section: Reprintsmentioning

confidence: 99%

“…amino-3-deoxy-2,4,6-tri-O-benzyl-␣-D-altro-hexopyranoside(7). A solution of 6 (0.45 g, 0.93 mmol) in methanol (3 mL) was stirred with 10% Pd/C for 4-5 h at room temperature under a hydrogen atmosphere, at atmospheric pressure.…”

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confidence: 99%

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PREPARATION AND REACTIVITY OF SOME 3-DEOXY-D-ALTRONIC ACID DERIVATIVES

Garcı́a-Martı́n

de-Paz

Galbis

2001

Journal of Carbohydrate Chemistry

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3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was the key intermediate in the preparation of poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl)propanamide], a chiral nylon 3 analog. We now describe an alternative synthetic route to this amino acid and the unexpected reactivity of some of its 3-deoxy derivatives. Attempts to open the 3-azido-3-deoxy-tri-O-methyl (or O-benzyl)-D-altrono-1,5-lactone intermediates gave mixtures of products, mostly, ␣,␤-unsaturated carbonyl compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Reprintsmentioning

confidence: 99%

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PREPARATION AND REACTIVITY OF SOME 3-DEOXY-D-ALTRONIC ACID DERIVATIVES

Garcı́a-Martı́n

de-Paz

Galbis

2001

Journal of Carbohydrate Chemistry

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“…Solvents were dried and purified when necessary, by appropriate standard procedures. 6‐Azido‐6‐deoxy‐2,3,4‐tri‐ O ‐methyl‐ d ‐glucono‐1,5‐lactone ( 8 ) and 6‐azido‐6‐deoxy‐2,3,4‐tri‐ O ‐benzyl‐ d ‐glucono‐1,5‐lactone ( 9 ) were obtained from O‐ methyl‐α‐ d ‐glucopyranoside in global yields of 45 and 40%, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…A solution of 6‐azido‐6‐deoxy‐2,3,4‐tri‐ O ‐methyl‐ d ‐glucono‐1,5‐lactone ( 8 ) (3.80 g, 15.49 mmol) and propargylamine (1.0 mL, 15.6 mmol) in dry methanol (5 mL) was refluxed for 2 h. The solvent was evaporated under reduced pressure and the residue was chromatographed on a silica gel column (eluent 2:1 hexane/ethyl acetate) to give 10 as a syrup (3.50 g, 75%).…”

Section: Methodsmentioning

confidence: 99%

Linear poly(amide triazole)s derived from d -glucose

Pinilla

Martı́nez

Hakkou

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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The click reaction between azides and alkynes is been increasingly employed in the preparation of polymers. In this article, we describe the synthesis and click polyaddition reaction of a new A‐B‐type amide monomer—prepared from d‐glucose as renewable resource—containing the alkyne and azide functions. Both Cu(I)‐catalyzed and metal‐free click polymerization methods were used to prepare glucose‐derived poly(amide triazole)s. The resulting polymers had weight‐average molecular weights in the 45,000–129,000 range and were characterized by GPC, IR, and NMR spectroscopies. Thermal and X‐ray diffraction studies revealed them to be amorphous. Their qualitative solubilities in various solvents and their water sorption have been studied. The poly(amide triazole)s having the alcohol functions protected as methyl ether were water‐soluble. The presence of the amide functions along the polymer chain made these polytriazoles degradable in the presence of sodium deuteroxide. The degradation was monitored by NMR analysis, and the degradation product was characterized by HRMS. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 629–638

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Diesterification of 3‐[(β‐Cyclodextrinyl)succinamido]propane‐1,2‐diol Catalysed by Lipase: Diastereoselectivity or Tridimensional Substrate Specificity?

et al. 2014

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The transesterification of 3‐[(β‐cyclodextrinyl)succinamido]propane‐1,2‐diol with fatty esters catalyzed by immobilized lipase from Mucor miehei occurred with very different conversions of the two diastereoisomers [(R)‐ or (S)‐amidopropanediol]. The highest conversion observed with the (S)‐amidopropanediol can be related to either lipase diastereoselectivity or substrate specificity. To investigate the diastereoselectivity of the lipase, diastereoisomers of the methylated β‐cyclodextrin were replaced by methylated glucopyranoside or methylleucine. No discrimation of the diastereoisomers by lipase was observed. Molecular modeling was performed to assess the lipase selectivity towards the two diastereoisomers. It was found that the (R)‐amidopropanediol is stabilized by hydrogen bonding with the cyclodextrin rim resulting in less reactive hydroxy groups.

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Some derivatives of 6-amino-6-deoxy-d-gluconic acid that are precursors for the synthesis of polyamides

Cited by 17 publications

References 5 publications

PREPARATION AND REACTIVITY OF SOME 3-DEOXY-D-ALTRONIC ACID DERIVATIVES

PREPARATION AND REACTIVITY OF SOME 3-DEOXY-D-ALTRONIC ACID DERIVATIVES

Linear poly(amide triazole)s derived from d -glucose

Diesterification of 3‐[(β‐Cyclodextrinyl)succinamido]propane‐1,2‐diol Catalysed by Lipase: Diastereoselectivity or Tridimensional Substrate Specificity?

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