2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose

Base Information

Chemical Name:2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose
CAS No.:1575814-82-2
Molecular Formula:C₃₅H₂₇F₃N₂O₈
Molecular Weight:660.603
Hs Code.:

Synonyms:2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose

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Chemical Property of 2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose

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Technology Process of 2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose

There total 8 articles about 2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose 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: 89.0%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 176640-04-3
3-[3-hydroxymethylphenyl]-3-trifluoromethyl-3H-diazirine

: 1575814-82-2
2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 2h;
DOI:10.1021/jo402738t

Reference yield:

: 167550-17-6
1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-iodo-benzene

: 1575814-82-2
2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.2: 1.25 h / -78 °C

2.1: pyridine; hydroxylamine hydrochloride / ethanol / 60 °C

3.1: triethylamine; dmap / dichloromethane / 20 °C

4.1: ammonia / methanol / 48 h / -78 - 20 °C / Sealed tube

5.1: triethylamine; iodine / methanol / 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -30 °C

With pyridine; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; ammonia; iodine; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane;
DOI:10.1021/jo402738t

Reference yield:

: 57455-06-8
3-iodobenzylalcohol

: 1575814-82-2
2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.2: 1.25 h / -78 °C

3.1: pyridine; hydroxylamine hydrochloride / ethanol / 60 °C

4.1: triethylamine; dmap / dichloromethane / 20 °C

5.1: ammonia / methanol / 48 h / -78 - 20 °C / Sealed tube

6.1: triethylamine; iodine / methanol / 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -30 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; ammonia; iodine; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo402738t