2013
DOI: 10.1155/2013/748161
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The Newest Member of the Family of Chloralose: Synthesis of β‐Ribochloralose and Some Derivatives

Abstract: 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 … Show more

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Cited by 3 publications
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“…15). 57 In this synthesis azidofuranoses 98-100 were synthesized by three processes, firstly protection of corresponding monosaccharides with either trichloroethylidene (for ribose) or isopropylidene (for mannose and glucose), after that the addition of a leaving group and its exchange with sodium azide [58][59][60][61] and propargylated nucleobases 101-104 62 were synthesized by the propargylation of nucleobases (uracil, thymine, 5-fluorouracil, and adenine) with propargyl bromide in the presence of K2CO3 in DMF solvents at 50 ᵒC for 8-12 h.…”
Section: Synopen Review / Short Reviewmentioning
confidence: 99%
See 1 more Smart Citation
“…15). 57 In this synthesis azidofuranoses 98-100 were synthesized by three processes, firstly protection of corresponding monosaccharides with either trichloroethylidene (for ribose) or isopropylidene (for mannose and glucose), after that the addition of a leaving group and its exchange with sodium azide [58][59][60][61] and propargylated nucleobases 101-104 62 were synthesized by the propargylation of nucleobases (uracil, thymine, 5-fluorouracil, and adenine) with propargyl bromide in the presence of K2CO3 in DMF solvents at 50 ᵒC for 8-12 h.…”
Section: Synopen Review / Short Reviewmentioning
confidence: 99%
“…Halay and co-workers synthesized triazolylmethyl-linked nucleoside derivatives 105 – 116 by click cycloaddition reaction of azidofuranoses 98 – 100 with propargylated nucleobases 101 – 104 in the presence of CuSO 4 ·5H 2 O and sodium ascorbate in the solvent THF/ t -BuOH/H 2 O (3:1:1) at 50 °C for 3–6 h (Scheme 15 ). 57 In this synthesis, azidofuranoses 98 – 100 were synthesized by three processes, firstly protection of corresponding monosaccharides with either trichloroethylidene (for ribose) or isopropylidene (for mannose and glucose), after that the addition of a leaving group and its exchange with sodium azide 58 59 60 61 and propargylated nucleobases 101 – 104 62 were synthesized by the propargylation of nucleobases (uracil, thymine, 5-fluorouracil, and adenine) with propargyl bromide in the presence of K 2 CO 3 in DMF solvents at 50 °C for 8–12 h.…”
Section: Cuaac Click Chemistry Mediated Synthesis Of Triazole-based G...mentioning
confidence: 99%