(4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide

Base Information

• Chemical Name: (4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide
• CAS No.: 585526-23-4
• Molecular Formula: C₂₃H₄₁NO₅Si
• Molecular Weight: 439.668
• Mol file: 585526-23-4.mol

Synonyms:(4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide

Chemical Property of (4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide

There total 7 articles about (4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide 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:

(2R,3S)-3-(4-Methoxy-benzyloxymethyl)-2-methyl-oxirane-2-carbaldehyde (585526-26-7) → (4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide (585526-23-4)

Guidance literature:

Multi-step reaction with 5 steps

1: benzene / 20 °C

2: 96 percent / Pd₂(dba)3*CHCl₃; n-Bu₃P; HCO₂H / triethylamine; dioxane

3: 99 percent / H₂ / Pd/C / ethyl acetate / 20 °C

4: Me₂AlCl / CH₂Cl₂ / 0 - 20 °C

5: imidazole; DMAP / dimethylformamide / 20 °C

With 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; tributylphosphine; hydrogen; dimethylaluminum chloride; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; ethyl acetate; triethylamine; N,N-dimethyl-formamide; benzene; 1: Wittig reaction;

DOI:10.1016/S0040-4039(03)01184-5

Reference yield:

[3-(4-methoxybenzyloxymethyl)-2-methyloxiranyl]methanol (167687-20-9) → (4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide (585526-23-4)

Guidance literature:

Multi-step reaction with 6 steps

1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

2: benzene / 20 °C

3: 96 percent / Pd₂(dba)3*CHCl₃; n-Bu₃P; HCO₂H / triethylamine; dioxane

4: 99 percent / H₂ / Pd/C / ethyl acetate / 20 °C

5: Me₂AlCl / CH₂Cl₂ / 0 - 20 °C

6: imidazole; DMAP / dimethylformamide / 20 °C

With 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; oxalyl dichloride; tributylphosphine; hydrogen; dimethylaluminum chloride; dimethyl sulfoxide; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; ethyl acetate; triethylamine; N,N-dimethyl-formamide; benzene; 2: Wittig reaction;

DOI:10.1016/S0040-4039(03)01184-5

Reference yield:

(2E)-4-[(4-methoxyphenyl)methoxy]-2-methylbut-2-en-1-ol (167687-19-6) → (4S,5R)-6-(4-Methoxy-benzyloxy)-4-methyl-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide (585526-23-4)

Guidance literature:

Multi-step reaction with 7 steps

1: (+)-DET; Ti(OiPr)4; tBuOOH / MS-4A / CH₂Cl₂ / -25 °C

2: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

3: benzene / 20 °C

4: 96 percent / Pd₂(dba)3*CHCl₃; n-Bu₃P; HCO₂H / triethylamine; dioxane

5: 99 percent / H₂ / Pd/C / ethyl acetate / 20 °C

6: Me₂AlCl / CH₂Cl₂ / 0 - 20 °C

7: imidazole; DMAP / dimethylformamide / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; oxalyl dichloride; diethyl (2R,3R)-tartrate; tributylphosphine; hydrogen; dimethylaluminum chloride; dimethyl sulfoxide; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; ethyl acetate; triethylamine; N,N-dimethyl-formamide; benzene; 3: Wittig reaction;

DOI:10.1016/S0040-4039(03)01184-5

upstream raw materials:

triethylsilyl chloride

(4S,5R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-4-methyl-hexanoic acid methoxy-methyl-amide

(2R,3S)-3-(4-Methoxy-benzyloxymethyl)-2-methyl-oxirane-2-carbaldehyde

(2E)-4-[(4-methoxyphenyl)methoxy]-2-methylbut-2-en-1-ol

Downstream raw materials:

(2R,3S,9S,10R)-2-(tert-Butyl-dimethyl-silanyloxy)-1,11-bis-(4-methoxy-benzyloxy)-3,9-dimethyl-10-triethylsilanyloxy-undec-4-yn-6-one

(2R,3S,9S,10R)-2-(tert-Butyl-dimethyl-silanyloxy)-1,11-bis-(4-methoxy-benzyloxy)-3,9-dimethyl-10-triethylsilanyloxy-undecan-6-one

tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane

Methanesulfonic acid (1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butyl ester