(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

Base Information

Chemical Name:(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide
CAS No.:612546-53-9
Molecular Formula:C₂₇H₅₂N₂O₅SSi₂
Molecular Weight:572.957
Hs Code.:

(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

Synonyms:(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

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Chemical Property of (2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

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Technology Process of (2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

There total 11 articles about (2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid 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: 87.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 612546-48-2
(2S,3R,4R)-5-Hydroxy-2-((R)-1-hydroxy-ethyl)-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

: 612546-53-9
(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1055/s-2003-39910

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 612546-53-9
(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

Guidance literature:: Multi-step reaction with 6 steps

1: methanol / 20 °C

2: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 0 °C

3: hexamethylphosphoric acid triamide / 20 °C

4: 91 percent / DIBAL / CH₂Cl₂ / -78 °C

5: 89 percent / H₂O₂; NH₄OH / ethanol / 20 °C

6: 87 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; dmap; ammonium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2003-39910

Reference yield:

: 612546-37-9
(Z)-(2R,5R)-6-Methoxymethoxy-5-methyl-hex-3-en-2-ol

: 612546-53-9
(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

Guidance literature:: Multi-step reaction with 9 steps

1.1: DBU / acetonitrile / 0 °C

2.1: IBr; DBU / CH₂Cl₂; acetonitrile / -78 - -50 °C

3.1: aq. HCl / methanol / 20 °C

3.2: NaHCO₃ / methanol / 20 °C

4.1: methanol / 20 °C

5.1: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 0 °C

6.1: hexamethylphosphoric acid triamide / 20 °C

7.1: 91 percent / DIBAL / CH₂Cl₂ / -78 °C

8.1: 89 percent / H₂O₂; NH₄OH / ethanol / 20 °C

9.1: 87 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; ammonium hydroxide; dihydrogen peroxide; iodine(I) bromide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1055/s-2003-39910