4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

Base Information

• Chemical Name: 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole
• CAS No.: 292073-56-4
• Molecular Formula: C₂₄H₃₁NO₂SSi
• Molecular Weight: 425.667
• Mol file: 292073-56-4.mol

Synonyms:4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

Chemical Property of 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

There total 14 articles about 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole 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%

methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-carboxylate (292073-46-2) → 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-56-4)

Guidance literature:

methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-carboxylate; With lithium aluminium tetrahydride; In diethyl ether; Inert atmosphere;

With water; In diethyl ether; Inert atmosphere;

DOI:10.1002/ejoc.201100669

Reference yield: 90.0%

ethyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-carboxylate (934989-89-6) → 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-56-4)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 ℃; for 1h;

DOI:10.1002/ejoc.200600671

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-56-4)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 14 h / 20 °C

2: DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

3: Et₃N; pyridine*SO₃; DMSO / CH₂Cl₂ / 0.33 h / 20 °C

4: 16.8 g / Et₃N / toluene / 12 h / 20 °C

5: 62 percent / chemical manganese dioxide; pyridine / benzene / 12 h / Heating

6: 91 percent / DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3: Parikh-Doering oxidation;

DOI:10.1016/S0040-4020(03)01020-2

upstream raw materials:

methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-carboxylate

ethyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-carboxylate

3-((tert-butyl(diphenyl)silyl)oxy)-2,2-dimethylpropanoic acid

3-(tert-butyldiphenylsilyloxy)-2,2-dimethylpropanamide

Downstream raw materials:

4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-prop-2-ynylthiazole

2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-hex-5-en-2-ynylthiazole

(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole