(3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one

Base Information

• Chemical Name: (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one
• CAS No.: 215798-01-9
• Molecular Formula: C₁₈H₂₈O₃Si
• Molecular Weight: 320.504
• Mol file: 215798-01-9.mol

Synonyms:(3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one

Chemical Property of (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one

There total 13 articles about (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one 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: 80.0%

(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl ester (210300-08-6) → (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one (215798-01-9)

Guidance literature:

In dichloromethane; at 25 ℃; for 72h;

DOI:10.1016/S0040-4020(98)00777-7

Reference yield: 68.0%

(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester (215797-95-8) → (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one (215798-01-9)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In dichloromethane; at 25 ℃; for 14h;

DOI:10.1016/S0040-4020(98)00777-7

Reference yield:

(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one (96837-44-4) → (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one (215798-01-9)

Guidance literature:

Multi-step reaction with 6 steps

2: 100 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 13 h / 25 °C

3: 89 percent / imidazole / dimethylformamide / 6 h / 25 °C

4: 56 percent / DMAP, EDCI*HCl / CH₂Cl₂ / 21 h / 25 °C

5: 100 percent / H₂ / Pd(OH)2/C / ethanol / 14 h / 25 °C / 3040 Torr

6: 68 percent / triethylamine, DMAP, 2,4,6-trichlorobenzoyl chloride / CH₂Cl₂ / 14 h / 25 °C

With 1H-imidazole; dmap; lithium hydroxide; 2,4,6-trichlorobenzoyl chloride; hydrogen; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00777-7

upstream raw materials:

(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester

(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl ester

tert-butyldimethylsilyl chloride

(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one

Downstream raw materials:

(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one