1,2-O-trichloroethylidene-α-d-galactofuranose

Anıl, Hüseyın; Yüceer, Levent; Yüceer, Tamara

doi:10.1016/0008-6215(83)88390-6

Cited by 20 publications

(9 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The low yield is attributed to the possibility of degradation of the sugar via the sulfuric acid catalyst. Pure single diastereomer (1) was obtained in 28% yield as a furanose form like all other chloralose molecules [3][4][5][6][7][8][9]. Although arabinochloralose [5], which is the diastereomer of 1, was purified from water or methanol, 1 was not crystallized from water or methanol because of dissolving.…”

Section: Resultsmentioning

confidence: 99%

“…The compound 1 was obtained as colorless crystals. Product 1 cannot be recrystallized from hot water or methanol due to dissolution unlike other chloraloses reported in literatures [5,8,9] (2). Acetic anhydride (1.35 mL, 0.0143 mol, d:1.08 g/mL, 4 eq.)…”

Section: 2-o-(s)-trichloroethylidene--d-ribofuranose ( -Ribochloralmentioning

confidence: 86%

“…The first members of this class are -andchloralose (or -glucochloralose) prepared via the reaction of anhydrous glucose and anhydrous chloral in the presence of sulfuric acid catalyst by Heffter [1] and the first time applied to therapeutics by Hanriot [2,3]. In addition to glucochloraloses, preparations of other chloraloses (xylochloralose [3,4], arabinochloralose [3,[5][6][7], galactochloralose [3,8] and mannochloralose [3,9]) have been also reported using the same synthetic method. All of chloraloses [3][4][5][6][7][8][9] synthesized so far contain 1,2-O-trichloroethylidene group in furanose form.…”

Section: Introductionmentioning

confidence: 99%

“…In addition to glucochloraloses, preparations of other chloraloses (xylochloralose [3,4], arabinochloralose [3,[5][6][7], galactochloralose [3,8] and mannochloralose [3,9]) have been also reported using the same synthetic method. All of chloraloses [3][4][5][6][7][8][9] synthesized so far contain 1,2-O-trichloroethylidene group in furanose form. Unlike most acetals, 1,2-O-trichloroethylidene acetals are very stable protecting group under acidic media because of inductive effects of trichloromethyl group and also stable in mild basic conditions.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The Newest Member of the Family of Chloralose: Synthesis of β‐Ribochloralose and Some Derivatives

Halay

2013

Journal of Chemistry

View full text Add to dashboard Cite

Treatment ofD-ribose with chloral in the presence of acid catalyst gives 1,2-O-(S)-trichloroethylidene-α-D-ribofuranose (1) (β-ribochloralose). Some derivatives of this product (1) were synthesized to be used as an intermediate in carbohydrate chemistry. Tricyclic orthoester structure (3, 77%) was obtained from the reaction of1with potassiumt-butoxide. This novel orthoester is expected to be useful as a glycosyl donor in the formations of new ribofuranoside units. 3-O-Methyl-ribochloralose (5) was synthesized in 75% yield via the methylation of1. 5-O-Tosyl-ribochloralose (6, 61%) was prepared with monotosylation reaction of1. Treatment of6with NaN3in DMF gives a 5-azido-5-deoxy-ribochloralose (7) in 77% yield. The azidosugar (7) was reduced to 5-amino-5-deoxy-ribochloralose (8, 72%) with triphenylphosphine according to Staudinger’s reduction procedure.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: 2-o-(s)-trichloroethylidene--d-ribofuranose ( -Ribochloralmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The Newest Member of the Family of Chloralose: Synthesis of β‐Ribochloralose and Some Derivatives

Halay

2013

Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…The procedure described for the preparation of the corresponding galactofuranose derivative [36] was thus investigated and adapted. Arabinose was treated with a large excess of anhydrous chloral in acidic medium to give 1,2-trichloroethylidene acetal 4 in 43% isolated yield after crystallization.…”

Section: Synthesis Of Orthoestersmentioning

confidence: 99%

Elaboration of Monoarabinofuranosidic Building Blocks

2002

View full text Add to dashboard Cite

Study of Radiotherapy Properties and Antimicrobial Activity of Glyconanoparticles (GNPs) Generated from Imidazolium Salts

et al. 2023

View full text Add to dashboard Cite

Carbohydrate‐based imidazolium salts (IMSs) are structural patterns for the synthesis of pharmaceutically and biologically active substances. For this purpose, the chiral furanoside‐based imidazolium salt conjugated with a cysteamine (Cyt) linker attached gold and silver nanoparticles were prepared in this study. The biological applications of the HeLa and A549 cell lines using MTT cell proliferation method were exhibited to determine the biological evaluation of NPs conjugated with sugar based imidazolium salt. The satisfactory results obtained demonstrated that the synthesized glyconanoconjugates were radiotherapeutic agents. Moreover, this modification type within a galactose derived imidazolium salt is the first work in bioapplications, especially in radiotherapy. The antimicrobial activity of IMSs and their nanoconjugates against test pathogens was also evaluated using the disc diffusion technique.

show abstract

1,2-O-trichloroethylidene-α-d-galactofuranose

Cited by 20 publications

References 4 publications

The Newest Member of the Family of Chloralose: Synthesis of β‐Ribochloralose and Some Derivatives

The Newest Member of the Family of Chloralose: Synthesis of β‐Ribochloralose and Some Derivatives

Elaboration of Monoarabinofuranosidic Building Blocks

Study of Radiotherapy Properties and Antimicrobial Activity of Glyconanoparticles (GNPs) Generated from Imidazolium Salts

Contact Info

Product

Resources

About