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

Base Information

• Chemical Name: 2-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose
• CAS No.: 1575814-85-5
• Molecular Formula: C₄₁H₄₇F₃N₂O₇Si
• Molecular Weight: 764.914
• Mol file: 1575814-85-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 2-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-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: 30.0%

1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose (1575814-83-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose (1575814-84-4) + 2-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose (1575814-85-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/jo402738t

Reference yield:

1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-iodo-benzene (167550-17-6) → 2-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose (1575814-85-5)

Guidance literature:

Multi-step reaction with 10 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

9.1: pyridine / 3 h / 20 °C

10.1: triethylamine / N,N-dimethyl-formamide / 12 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; N,N-dimethyl-formamide;

DOI:10.1021/jo402738t

Reference yield:

2,3,5-tri-O-benzoyl-1-O-[3-(3-trifluoromethyl-3H-diazirine-3-yl)benzyl]-β-D-ribofuranose (1575814-82-2) → 2-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose (1575814-85-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine / 3 h / 20 °C

3: triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C

With pyridine; sodium methylate; triethylamine; In methanol; N,N-dimethyl-formamide;

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

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

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