(+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide

Base Information

• Chemical Name: (+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide
• CAS No.: 151058-21-8
• Molecular Formula: C₂₃H₄₁NO₅Si
• Molecular Weight: 439.668
• Mol file: 151058-21-8.mol

Synonyms:(+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide

Chemical Property of (+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide

There total 4 articles about (+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide 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: 95.0%

p-Methoxybenzyl bromide (2746-25-0) + (2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoic acid methoxy-methyl-amide (151058-20-7) → (+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide (151058-21-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00074a005

Reference yield: 60.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (+)-[2S-(2R*,3S*,4S*)]-5-hydroxy-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide (151058-22-9) → (+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide (151058-21-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo101598y

Reference yield:

(2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal (97826-89-6) → (+)-[2S-(2R*,3S*,4S*)]-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide (151058-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / n-Bu₂BOTf, Et₃N / CH₂Cl₂

2: 91 percent / AlMe₃ / tetrahydrofuran

3: 95 percent / NaH / dimethylformamide

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00074a005

upstream raw materials:

p-Methoxybenzyl bromide

(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoic acid methoxy-methyl-amide

(2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal

(S)-4-Benzyl-3-[(2S,3R,4R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

Downstream raw materials:

(+)-[2S-(2R*,3S*,4S*)]-5-hydroxy-3-[(4-methoxyphenyl)methoxy]-N-methoxy-N-2,4-trimethylpentanamide

(3S,4R,5R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-one

1-{(1R,2S)-1-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-3-trimethylsilanyloxy-but-3-enyloxymethyl}-4-methoxy-benzene

(2R,5S,6R,7R)-1-[(2S,4R,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one