1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

Base Information

Chemical Name:1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole
CAS No.:1416717-99-1
Molecular Formula:C₂₉H₂₆N₄O₇
Molecular Weight:542.548
Hs Code.:

Synonyms:1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

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Chemical Property of 1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

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Technology Process of 1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

There total 5 articles about 1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole 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: 93.23%

: 937-31-5
(4-Nitrophenyl)acetylene

: 234106-08-2
(2R,3S)-5β-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate

: 1416717-99-1
1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

Guidance literature:: With copper(II) sulfate; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; at 75 - 80 ℃; Inert atmosphere;
DOI:10.1021/jo302033f

Reference yield:

: 51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9
1-O-methyl-2-deoxy-D-ribofuranoside

: 1416717-99-1
1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

Guidance literature:: Multi-step reaction with 4 steps

1: dmap; pyridine / 12 h / 0 °C

2: hydrogenchloride / diethyl ether / 0 °C

3: boron trifluoride diethyl etherate; trimethylsilylazide / dichloromethane / 0 °C

4: sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; copper(II) sulfate / tetrahydrofuran; water / 75 - 80 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; trimethylsilylazide; boron trifluoride diethyl etherate; copper(II) sulfate; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1021/jo302033f

Reference yield:

: 4330-34-1
methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

: 1416717-99-1
1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

Guidance literature:: Multi-step reaction with 3 steps

1: hydrogenchloride / diethyl ether / 0 °C

2: boron trifluoride diethyl etherate; trimethylsilylazide / dichloromethane / 0 °C

3: sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; copper(II) sulfate / tetrahydrofuran; water / 75 - 80 °C / Inert atmosphere

With hydrogenchloride; trimethylsilylazide; boron trifluoride diethyl etherate; copper(II) sulfate; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1021/jo302033f