tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane

Base Information

• Chemical Name: tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane
• CAS No.: 255912-54-0
• Molecular Formula: C₁₇H₂₅NO₄Si
• Molecular Weight: 335.475
• Mol file: 255912-54-0.mol

Synonyms:tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane

Chemical Property of tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane

There total 3 articles about tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane 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: 93.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,4S)-2-(4-Nitro-phenyl)-3,4-dihydro-2H-pyran-4-ol (255912-53-9) → tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane (255912-54-0)

Guidance literature:

With triethylamine; In dichloromethane; for 2h;

DOI:10.1016/S0040-4039(99)01832-8

Reference yield:

(2S)-2-(4-nitrophenyl)-2,3-dihydro-4H-pyran-4-one (162299-82-3) → tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane (255912-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaBH₄; CeCl₃ / methanol; ethanol / 6 h / -78 - 20 °C

2: 93 percent / Et₃N / CH₂Cl₂ / 2 h

With sodium tetrahydroborate; cerium(III) chloride; triethylamine; In methanol; ethanol; dichloromethane; 1: Luche reduction / 2: silylation;

DOI:10.1016/S0040-4039(99)01832-8

Reference yield:

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester (162181-12-6) → tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane (255912-54-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / CF₃COOH / CH₂Cl₂ / 0.5 h

2: 80 percent / NaBH₄; CeCl₃ / methanol; ethanol / 6 h / -78 - 20 °C

3: 93 percent / Et₃N / CH₂Cl₂ / 2 h

With sodium tetrahydroborate; cerium(III) chloride; triethylamine; trifluoroacetic acid; In methanol; ethanol; dichloromethane; 1: Elimination / 2: Luche reduction / 3: silylation;

DOI:10.1016/S0040-4039(99)01832-8

upstream raw materials:

t-butyldimethylsiyl triflate

(2S,4S)-2-(4-Nitro-phenyl)-3,4-dihydro-2H-pyran-4-ol

(2S)-2-(4-nitrophenyl)-2,3-dihydro-4H-pyran-4-one

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester