Expeditious synthesis of enantiopure symmetrical macroheterocycles by ring-closing metathesis of ether and tether-linked 1,2-O-isopropylidenefuranosides

Biswas, Goutam; Sengupta, Jhimli; Nath, Madhumita; Bhattacharjya, Anup

doi:10.1016/j.carres.2004.12.024

Cited by 7 publications

(5 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Successive 5, 6-deprotection, oxidation and finally reduction gave compound 5. 30 A 24 membered C2-symmetric macrocycle CSM-1 (59%) was obtained from 5 following the same etherification technique (Scheme 1). The symmetric character of the product CSM-1 was indicated by the presence of one set of peaks due to symmetry of the related protons and carbon atoms in the 1 H-NMR and 13 C-NMR spectra.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of C2-symmetric carbohydrate-based macrocycles by introduction of methylene/p-xylene linkers

Sengupta¹,

Hudait²,

Bhuyan³

et al. 2022

Arkivoc

Self Cite

View full text Add to dashboard Cite

Over the last few decades many carbohydrate embedded macrocycles have drawn the attention of synthetic organic chemists because of their interesting chemical and biological properties. Suitably placed chiral 3-and 5-hydroxyl groups of 1,2-O-(1-methylethylidene)-α-D-xylofuranose, derived from inexpensive D-glucose, have been judiciously exploited to generate different non-natural C2-symmetric carbohydrate embedded macrocycles. Different symmetric aromatic and aliphatic hydrophobic spacers have been introduced between highly functionalized cluster of carbohydrate chiral centres through different intra-and intermolecular nucleophilic substitution and ring closing metathesis (RCM) for synthesis of 17 to 24 membered C2-symmetric macrocycles.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of C2-symmetric carbohydrate-based macrocycles by introduction of methylene/p-xylene linkers

Sengupta¹,

Hudait²,

Bhuyan³

et al. 2022

Arkivoc

Self Cite

View full text Add to dashboard Cite

show abstract

“…This product has recently been prepared from compound 2 by means of a similar onestep proce dure, but no experimental details and characterization have been furnished [38]. Phosphor tribromide in dry diethyl ether was added dropwise to a cooled (3 °C) dry diethyl ether/ethyl acetate solution.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, characterization and computational investigation of novel metalloporphyrazines containing 15-membered O2S2-donor macrocyclic moieties

Bayğu

Yıldız

Kara

et al. 2018

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

New metalloporphyrazines (MgPz, ZnPz) containing peripheral tetrasubstitutions derived from 7,8dihydro6H,14H,19Hdibenzo[bj] [1,12,5,8]dioxadithiacyclopentadecine16,17dicarbonitrile (6) have been synthesized by a multistep reaction sequence and characterized. Compound 6 has been prepared by the reaction of 1,3di(2bromomethyl phenoxy) propane (3) or 1,3di(2iodomethylphenoxy) propane (4) which were prepared via bromination or iodination of {2[3(2hydroxymethylphenoxy) propoxy]phenyl} methanol (2) and cis1,2dicyano1,2ethylenedithiolate (5). The novel magnesium porphyrazine was prepared by the cyclotetramerization reaction of 6 with magnesium butoxide. The onestep synthesis of porphyrazinato zinc complex has been achieved without a reaction sequence by using dicyano compound (6) and zinc butoxide. The prediction of the geometry optimization, normal mode frequencies, 1 H, 13 C NMR, UV absorption spectra, chemical shifts, electronic properties and NBO analysis of the compound were examined by using B3LYP method with a 631G(d, p) basis set. These novel compounds were characterized by a combination of elemental analysis, 1 H, 13 C NMR, FTIR, UVvis and MS spectral data. An Xray crystal structure of dicarbodinitrile compound (6) was also investigated.

show abstract

“…41, were coupled with nucleophiles under basic conditions in water (NaOH 11%, (nBu) 4 NBr with heating for extended time) to give the ethers (e.g. 42) in good yield (Scheme 11) [27][28][29]. An excess of the mesylate was required, and the elimination product was also observed.…”

Section: Alkylationmentioning

confidence: 99%

“…An excess of the mesylate was required, and the elimination product was also observed. Primary and secondary carbohydrate alcohols were both used as nucleophiles, giving (5-5)-linked [27] and (3-5)-linked [28,29] ethers.…”

Section: Alkylationmentioning

confidence: 99%

Neodisaccharide diglycosyl compounds: Ethers, thioethers and selenoethers. A survey of their synthesis and biological activity

Cumpstey

2010

Comptes Rendus. Chimie

View full text Add to dashboard Cite

show abstract

Expeditious synthesis of enantiopure symmetrical macroheterocycles by ring-closing metathesis of ether and tether-linked 1,2-O-isopropylidenefuranosides

Cited by 7 publications

References 33 publications

Synthesis of C2-symmetric carbohydrate-based macrocycles by introduction of methylene/p-xylene linkers

Synthesis of C2-symmetric carbohydrate-based macrocycles by introduction of methylene/p-xylene linkers

Synthesis, characterization and computational investigation of novel metalloporphyrazines containing 15-membered O2S2-donor macrocyclic moieties

Neodisaccharide diglycosyl compounds: Ethers, thioethers and selenoethers. A survey of their synthesis and biological activity

Contact Info

Product

Resources

About