Synthesis of d-mannitol and l-iditol derivatives as monomers for the preparation of new regioregular AABB-type polyamides

Mancera, Manuel; Roffé, Isaac; Rivas, M. Verónica; Silva, Cármen; Galbis, Juan A.

doi:10.1016/s0008-6215(02)00040-x

Cited by 20 publications

(14 citation statements)

References 10 publications

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“…Thus, oxidation of the alditol to aldaric acids, followed by methylation, ammonolysis to the diamides, then followed by reduction to diamines yielded a complex product mixture. [12] Sulfonylation of an alditol [13] followed by azidation gave a mixture of products in low yield. Therefore, we devised a strategy related to the one by Galbis et al [11] but starting from alditols (Schemes 3 and 4).…”

Section: Resultsmentioning

confidence: 99%

“…The formation of cyclic ethers by demethylative cyclization can be avoided by minimizing the contact with typical chromatographic stationary phases. 13 C, COSY, [20] PE COSY, [21] gHSQC, [22] gHMBC, [23] ROESY, [24] and TOCSY [25] spectra. For NMR spectroscopic titrations, aliquots of ligand solution were added to a solution of clip 1 in an NMR spectroscopy tube.…”

Section: Resultsmentioning

confidence: 99%

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Improved Stereochemical Analysis of Conformationally Flexible Diamines by Binding to a Bisporphyrin Molecular Clip

Norrehed

Johansson

Grennberg

et al. 2013

Chemistry A European J

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The relative stereochemistry of acyclic diamines with several stereogenic centers has been analyzed by NMR spectroscopy in combination with conformational deconvolution. Binding to a bisporphyrin molecular clip improves the stereochemical assignment significantly. The diamines were synthesized from inexpensive sugar alcohols, and their stable hydrochlorides were quantitatively converted into free bases by treatment with ion-exchange resin.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Improved Stereochemical Analysis of Conformationally Flexible Diamines by Binding to a Bisporphyrin Molecular Clip

Norrehed

Johansson

Grennberg

et al. 2013

Chemistry A European J

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“…The synthesis of diamines 5 and 6 and their dihydrochlorides (7,8) from D-mannitol, was described in full detail in a preceding paper. 8 The diamino compounds 3 and 4 were obtained from the corresponding diazido derivatives 1 and 2 by catalytic hydrogenation in methanol (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of New Stereoregular AABB-Type Polyamides from Carbohydrate-based Monomers Having d-manno and l-ido Configurations

et al. 2003

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Polycondensation of 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-D-mannitol or 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-L-iditol with aromatic and aliphatic dicarboxylic acids has been used to prepare a series of regio-and stereoregular AABB-type polyamides. We also describe the preparation of 1,6-diamino-1,6-dideoxy-3,4-O-isopropylidene-D-mannitol and 1,6-diamino-1,6-dideoxy-2,5-di-O-methyl-3,4-O-isopropylidene-D-mannitol and their polycondensation reactions with the same dicarboxylic acids. The obtained polyamides were gummy solids that were optically active and had a pronounced affinity for water, although most of them were not soluble in this solvent. These polyamides were characterized by viscosimetry, gel-permeation chromatography, elemental analysis, and IR and NMR spectroscopies.

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“…In the synthesis of GA-based polymers with linear structures, four hydroxyl groups need to be protected to prevent undesired side reactions and to allow polymerization with counter monomers through carboxyl groups. There have been several studies of the syntheses of aldaric acid-based monomers and their polymers via various synthetic routes, e.g., galactaric acid acetate and its polyamides , and polyanhydrides, methyl tartaric acid and its polyamides, methyl mannaric and galactaric acids and their polyamides, ,− methyl arabinaric and xylaric acids and their polyamides, , and acetal galactaric acid and its polyesters . Various polymers were obtained by polycondensations of these aldaric-based monomers with aliphatic or aromatic diols and diamines using various methods, including solution, interfacial, and bulk polymerization.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Crystalline and Amphiphilic Polymers from d-Glucaric Acid

Enomoto-Rogers

Masaki

et al. 2016

ACS Sustainable Chem. Eng.

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D-Glucaric acid (GA), an aldaric acid isolated from various vegetables and fruits, is an important biobased building block. Glucaric acid acetate (GAA), which is acyclic, was synthesized in an acetic anhydride/sulfuric acid mixture. GAA was converted to glucaric acid chloride acetate (GACA) and then polymerized with various diols and diamines in dimethylacetamide solution or by interfacial polymerization in water and chloroform solutions. The polyesters and polyamides were amphiphilic and soluble in water and common organic solvents. The weight-average molecular weights of the polyesters were (0.4−0.7) × 10 3 ; those of the polyamides obtained by solution and interfacial polymerizations were (5.9− 8.0) × 10 3 and (14.5−20.8) × 10 3 , respectively. Differential scanning calorimetry showed that the polyamides were thermoplastic and melted at ca. 140°C, indicating crystallinity; the melting points increased with increasing number of diamine alkyl carbons. Novel biobased crystalline amphiphilic polymers were synthesized from GA.

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Synthesis of d-mannitol and l-iditol derivatives as monomers for the preparation of new regioregular AABB-type polyamides

Cited by 20 publications

References 10 publications

Improved Stereochemical Analysis of Conformationally Flexible Diamines by Binding to a Bisporphyrin Molecular Clip

Improved Stereochemical Analysis of Conformationally Flexible Diamines by Binding to a Bisporphyrin Molecular Clip

Synthesis and Characterization of New Stereoregular AABB-Type Polyamides from Carbohydrate-based Monomers Having d-manno and l-ido Configurations

Synthesis of Crystalline and Amphiphilic Polymers from d-Glucaric Acid

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