(4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal

Base Information

• Chemical Name: (4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal
• CAS No.: 115043-58-8
• Molecular Formula: C₁₉H₃₂O₃Si
• Molecular Weight: 336.547
• Mol file: 115043-58-8.mol

Synonyms:(4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal

Chemical Property of (4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal

There total 8 articles about (4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal 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%

(4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol → (4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal (115043-58-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1016/j.tetlet.2005.03.102

Reference yield:

((2S,3S)-2-benzyloxy-hex-5-en-3-yloxy)(tert-butyl)dimethylsilane (115043-57-7) → (4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal (115043-58-8)

Guidance literature:

With pyridinium chlorochromate; dimeric 9-borabicyclo[3.3.1]nonane; Yield given. Multistep reaction; 1.) CH₂Cl₂, 22 deg C, 30 min, reflux, 1.75 h, 2.) -40 deg C - reflux, 2.5 h;

DOI:10.1016/S0040-4039(00)96515-8

Reference yield:

(S)-2-(benzyloxy)propanal (81445-44-5) → (4S,5S)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-hexanal (115043-58-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: MgBr₂*Et₂O / CH₂Cl₂ / -78 °C

2.1: imidazole; DMAP / dimethylformamide

3.1: BH₃*SMe₂ / various solvent(s); tetrahydrofuran

3.2: 81 percent / NaOH; H₂O₂ / 50 °C

4.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂

With 1H-imidazole; dmap; dimethylsulfide borane complex; Dess-Martin periodane; magnesium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;

DOI:10.1016/j.tetlet.2005.03.102

upstream raw materials:

((2S,3S)-2-benzyloxy-hex-5-en-3-yloxy)(tert-butyl)dimethylsilane

(S)-2-(benzyloxy)propanal

(4S,5S)-5-(phenylmethoxy)hex-1-en-4-ol

benzyl bromide