1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose

Base Information

• Chemical Name: 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose
• CAS No.: 1575814-80-0
• Molecular Formula: C₁₄H₁₅F₃N₂O₅
• Molecular Weight: 348.279
• Mol file: 1575814-80-0.mol

Synonyms:1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose

Chemical Property of 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose

There total 10 articles about 1-O-[3-(3-trifluoromethyl-3H-diazirin-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: 95.0%

2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose (1575814-82-2) → 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose (1575814-80-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jo402738t

Reference yield:

1-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,2,2-trifluoroethanone (176640-03-2) → 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose (1575814-80-0)

Guidance literature:

Multi-step reaction with 7 steps

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

2: triethylamine; dmap / dichloromethane / 20 °C

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

4: triethylamine; iodine / methanol / 20 °C

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

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

7: sodium methylate / methanol / 2 h / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; ammonia; iodine; sodium methylate; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jo402738t

Reference yield:

1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-iodo-benzene (167550-17-6) → 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose (1575814-80-0)

Guidance literature:

Multi-step reaction with 8 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

8.1: sodium methylate / methanol / 2 h / 20 °C

With pyridine; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; ammonia; iodine; sodium methylate; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane;

DOI:10.1021/jo402738t

upstream raw materials:

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

1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-iodo-benzene

3-iodobenzylalcohol

1-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,2,2-trifluoroethanone

Downstream raw materials:

3-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose

2-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose

2-O-(tert-butyldimethyl)silyl-1-O-[3-(3-trifluoromethyl-3Hdiazirin-3-yl)]benzyl-5-O-(4,4′-dimethoxy)trityl-3-O-[(2-cyanoethoxy)(N,N-diisopropyamino)]phosphanyl-β-D-ribofuranose

1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose