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

Base Information

• Chemical Name: (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid
• CAS No.: 215797-96-9
• Molecular Formula: C₂₅H₃₆O₄Si
• Molecular Weight: 428.644
• Mol file: 215797-96-9.mol

Synonyms:(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid

Chemical Property of (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid

There total 4 articles about (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid 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: 89.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R,4S)-2-benzyl-3-hydroxy-4-benzyloxypentanoic acid (215798-07-5) → (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid (215797-96-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 6h;

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

Reference yield:

(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one (96837-44-4) → (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid (215797-96-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

With 1H-imidazole; lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

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

Reference yield:

hydrocinnamic acid chloride (645-45-4) → (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-benzyloxypentanoic acid (215797-96-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / n-butyllithium / tetrahydrofuran / 3 h / -78 °C

3: 100 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 13 h / 25 °C

4: 89 percent / imidazole / dimethylformamide / 6 h / 25 °C

With 1H-imidazole; lithium hydroxide; n-butyllithium; dihydrogen peroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

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

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3R,4S)-2-benzyl-3-hydroxy-4-benzyloxypentanoic acid

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

hydrocinnamic acid chloride

Downstream raw materials:

(2R,3R,4S)-2-Benzyl-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid (S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl ester

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

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

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