5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate

Base Information

• Chemical Name: 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate
• CAS No.: 187458-07-7
• Molecular Formula: C₁₃H₂₆O₄Si
• Molecular Weight: 274.433
• Mol file: 187458-07-7.mol

Synonyms:5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate

Chemical Property of 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate

There total 1 articles about 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate (187458-07-7)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide

2: 100 percent / Dibal-H / CH₂Cl₂; hexane / 3 h / -78 °C

3: 96 percent / pyridine; CH₂Cl₂ / 48 h

With 1H-imidazole; diisobutylaluminium hydride; In pyridine; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo982259u

Reference yield:

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate (187458-07-7) → 2',3'-Dideoxyuridine (5983-09-5,153547-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ethylaluminum dichloride / 1,2-dichloro-ethane; toluene / 16 h / 20 °C / Inert atmosphere; Cooling with ice

2: tetrabutyl ammonium fluoride / tetrahydrofuran

With tetrabutyl ammonium fluoride; ethylaluminum dichloride; In tetrahydrofuran; 1,2-dichloro-ethane; toluene;

DOI:10.1016/j.chembiol.2019.04.010

Reference yield:

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate (187458-07-7) → 2',3'-dideoxy-β-D-5-azacytidine (107036-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 20 percent / ethylaluminum dichloride / CH₂Cl₂; toluene / Ambient temperature

2: 36 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With tetrabutyl ammonium fluoride; ethylaluminum dichloride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/0040-4020(94)00997-9

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

tert-butyl<<(S)-2,3-dihydro-4-(phenylthio)-2-furyl>methoxy>dimethylsilane

tert-butyl<<(S)-2,3-dihydro-4-(phenylseleno)-2-furyl>methoxy>dimethylsilane

2',3'-dideoxy-β-D-5-azacytidine

9-(2,3-dideoxy-β-D-ribofuranosyl)-6-(methylthio)purine

Refernces

• 1、 Paquette, Leo A.,Brand, Stephen,Behrens, Carsten. "An enantioselective ring expansion route leading to furanose and pyranose nucleosides featuring spirodiketopiperazines at the anomeric position". . p. 2010 - 2025. Retrieved 2007/10/03.