methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate

Base Information

• Chemical Name: methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate
• CAS No.: 157494-64-9
• Molecular Formula: C₁₈H₃₀O₄Si
• Molecular Weight: 338.519
• Mol file: 157494-64-9.mol

Synonyms:methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate

Chemical Property of methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate

There total 1 articles about methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate 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:

benzyl bromide (100-39-0) + methyl (S)-4-<(1,1-dimethylethyl)dimethylsiloxy>-3-hydroxybutanoate (113494-89-6) → methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate (157494-64-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, hexane, -60 - -50 deg C, 30 min, 2.) -20 deg C, 1 h;

DOI:10.1039/P19940001833

Reference yield: 85.0%

methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate (157494-64-9) → cis-3-benzyl-4-hydroxytetrahydrofuran-2-one (157544-61-1)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; at 80 ℃; for 0.5h;

DOI:10.1039/P19940001833

Reference yield:

methyl (2R,3S)-2-benzyl-4-(tert-butyldimethylsiloxy)-3-hydroxybutanoate (157494-64-9) → (E)-benzylidenedihydro-2(3H)-furanone (6285-99-0,30959-91-2,40011-26-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / aq. HCl / dimethylformamide / 0.5 h / 80 °C

2: 95 percent / POCl₃ / pyridine / 1 h / 0 °C

3: 20 percent / 1,4-diazabicyclo<2.2.2>octane / methanol / 23 h / Irradiation

4: 1.) lithium N-isopropylcyclohexylamide / 1.) THF, hexane, 0 deg C, 30 min, 2.) 0 deg C, 1 h

5: NaIO₄ / 1.) THF, H₂O, room temperature, 12 h, 2.) toluene, reflux, 10 min

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium periodate; lithium cyclohexylisopropylamide; trichlorophosphate; In pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1039/P19940001833

upstream raw materials:

benzyl bromide

methyl (S)-4-<(1,1-dimethylethyl)dimethylsiloxy>-3-hydroxybutanoate

Downstream raw materials:

cis-3-benzyl-4-hydroxytetrahydrofuran-2-one

3-(phenylmethyl)-2(5H)-furanone

(E)-benzylidenedihydro-2(3H)-furanone

trans-3-benzyl-4-(hydroxymethyl)tetrahydrofuran-2-one