3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine

Base Information

• Chemical Name: 3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine
• CAS No.: 162844-91-9
• Molecular Formula: C₁₅H₂₁F₃N₂OSi
• Molecular Weight: 330.425
• Mol file: 162844-91-9.mol

Synonyms:3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine

Chemical Property of 3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine

There total 10 articles about 3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine 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: 86.0%

3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)diaziridine (162844-90-8) → 3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine (162844-91-9)

Guidance literature:

3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)diaziridine; With tert-butylhypochlorite; In methanol; at -70 ℃; for 0.166667h;

With sodium hydrogencarbonate; In methanol; at -70 - 20 ℃; for 2h;

DOI:10.1016/j.chembiol.2019.03.008

Reference yield:

1-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,2,2-trifluoroethanone O-tosyl oxime (162844-89-5) → 3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine (162844-91-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: triethylamine; iodine / methanol / 20 °C

With ammonia; iodine; triethylamine; In methanol;

DOI:10.1021/jo402738t

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3-(3-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine (162844-91-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / DBU

2: 1.) BuLi / 1.) THF, -78 deg C

3: 91 percent / NH₂OH*HCl / pyridine

4: 98 percent / NEt₃, DMAP

5: 92 percent / NH₃

6: t-BuOCl

With dmap; n-butyllithium; tert-butylhypochlorite; hydroxylamine hydrochloride; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In pyridine;

DOI:10.1016/0960-894X(96)00075-3

upstream raw materials:

(3-Bromophenyl)methanol

tert-butyldimethylsilyl chloride

[(3-bromobenzyl)oxy](tert-butyl)dimethylsilane

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

Downstream 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

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