1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

Base Information

Chemical Name:1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide
CAS No.:1321591-92-7
Molecular Formula:C₂₁H₂₂N₄O₆
Molecular Weight:426.429
Hs Code.:

Synonyms:1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

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Chemical Property of 1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

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Technology Process of 1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

There total 4 articles about 1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

: 1321591-87-0
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-iodo-1H-[1,2,3]triazole-4-carboxylic acid amide

: 536-74-3
phenylacetylene

: 1321591-91-6
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

: 1321591-92-7
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

Guidance literature:: With bis(benzonitrile)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 100 ℃;
DOI:10.1016/j.bmc.2011.05.050

Reference yield:

: 5975-09-7
2,3-O-isopropylidene-β-D-ribofuranosyl-1-azide

: 1321591-91-6
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

: 1321591-92-7
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

Guidance literature:: Multi-step reaction with 4 steps

1: potassium hydroxide / water; N,N-dimethyl-formamide / 5 h / 0 - 20 °C

2: pyridine / 20 °C

3: diiodomethane; isopentyl nitrite / 1.5 h / 110 °C

4: bis(benzonitrile)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 100 °C

With pyridine; bis(benzonitrile)palladium(II) dichloride; diiodomethane; potassium carbonate; potassium hydroxide; isopentyl nitrite; In 1,4-dioxane; water; N,N-dimethyl-formamide; 4: Sonogashira coupling;
DOI:10.1016/j.bmc.2011.05.050

Reference yield:

: 1321591-86-9
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-amino-1H-[1,2,3]triazole-4-carboxylic acid amide

: 1321591-91-6
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

: 1321591-92-7
1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(phenylethynyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

Guidance literature:: Multi-step reaction with 2 steps

1: diiodomethane; isopentyl nitrite / 1.5 h / 110 °C

2: bis(benzonitrile)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 100 °C

With bis(benzonitrile)palladium(II) dichloride; diiodomethane; potassium carbonate; isopentyl nitrite; In 1,4-dioxane; 2: Sonogashira coupling;
DOI:10.1016/j.bmc.2011.05.050