(RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine

Base Information

• Chemical Name: (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine
• CAS No.: 348128-69-8
• Molecular Formula: C₃₂H₄₄N₂O₅Si
• Molecular Weight: 564.797
• Mol file: 348128-69-8.mol

Synonyms:(RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine

Chemical Property of (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine

There total 11 articles about (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-[3-(tert-butyl-diphenyl-silanyloxymethyl)-6-dimethoxymethyl-pyridin-2-yl]-ethylamine (348128-68-7) → (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine (348128-69-8)

Guidance literature:

With triethylamine; In chloroform;

DOI:10.1246/cl.2001.380

Reference yield:

3-cyano-6-(dimethoxymethyl)-2-pyridone (156459-19-7) → (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine (348128-69-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 6M KOH / ethanol / 8 h / Heating

2: 7.73 mg / p-toluenesulfonic acid hydrate / Heating

3: 81 percent / DMAP / pyridine / 0.5 h / 0 °C

4: Pd(OAc)2; dppp; Et₃N / toluene / 6 h / Heating

5: 1.28 g / 70 percent AcOH / tetrahydrofuran / 20 °C

6: 94 percent / CaCl₂; NaBH₄ / ethanol / 3.5 h / 0 - 20 °C

7: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 20 °C

8: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

9: 0.42 g / NaN₃ / dimethylformamide / 0.5 h / 20 °C

10: H₂ / 10 percent Pd-C / ethanol / 0.5 h / 20 °C

11: 1.14 g / Et₃N / CHCl₃ / 4.5 h / 0 - 20 °C

With dmap; palladium diacetate; potassium hydroxide; sodium tetrahydroborate; sodium azide; 1,3-bis-(diphenylphosphino)propane; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.75.1583

Reference yield:

6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (156459-20-0) → (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine (348128-69-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 7.73 mg / p-toluenesulfonic acid hydrate / Heating

2: 81 percent / DMAP / pyridine / 0.5 h / 0 °C

3: Pd(OAc)2; dppp; Et₃N / toluene / 6 h / Heating

4: 1.28 g / 70 percent AcOH / tetrahydrofuran / 20 °C

5: 94 percent / CaCl₂; NaBH₄ / ethanol / 3.5 h / 0 - 20 °C

6: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 - 20 °C

7: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

8: 0.42 g / NaN₃ / dimethylformamide / 0.5 h / 20 °C

9: H₂ / 10 percent Pd-C / ethanol / 0.5 h / 20 °C

10: 1.14 g / Et₃N / CHCl₃ / 4.5 h / 0 - 20 °C

With dmap; palladium diacetate; sodium tetrahydroborate; sodium azide; 1,3-bis-(diphenylphosphino)propane; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.75.1583

upstream raw materials:

di-tert-butyl dicarbonate

1-[3-(tert-butyl-diphenyl-silanyloxymethyl)-6-dimethoxymethyl-pyridin-2-yl]-ethylamine

3-cyano-6-(dimethoxymethyl)-2-pyridone

6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid

Downstream raw materials:

phenacyl (RS)-2-(1H-2-t-butoxycarbonyl-1-oxo-2,3-dihydropyrrolo[3,4-b]pyridin-5-yl)-1,3-thiazole-4-carboxylate

phenacyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(hydroxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate

methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate

(RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylic acid