(2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

Base Information

Chemical Name:(2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate
CAS No.:913256-72-1
Molecular Formula:C₃₆H₅₅NO₇Si
Molecular Weight:641.921
Hs Code.:

Synonyms:(2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

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Chemical Property of (2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

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Technology Process of (2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

There total 9 articles about (2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate 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: 37.0%

: 913256-76-5
(2S,4R)-tert-butyl 2-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

: 24424-99-5
di-tert-butyl dicarbonate

: 913256-72-1
(2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

Guidance literature:: With dmap; triethylamine; In 1,4-dioxane; at 100 ℃; for 12h;
DOI:10.1002/ejoc.200600154

Reference yield:

: 92817-88-4
(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

: 913256-72-1
(2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 70 percent / (i-Pr)2NEt; LiCl / acetonitrile / 24 h / 20 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C

3.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -80 °C

3.2: trisyl azide / tetrahydrofuran; toluene / 0.07 h / -80 °C

3.3: 68 percent / acetic acid / tetrahydrofuran; toluene / -80 - 20 °C

4.1: 99 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

5.1: 92 percent / LiOH; aq. H₂O₂ / tetrahydrofuran; H₂O / 20 h / 24 °C

6.1: 75 percent / DMAP; Boc₂O / 0.5 h / 20 °C

7.1: 37 percent / DMAP; Et₃N / dioxane / 12 h / 100 °C

With dmap; lithium hydroxide; di-tert-butyl dicarbonate; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1002/ejoc.200600154

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 913256-72-1
(2S,4R)-tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-5-tert-butyldiphenylsilyloxy-4-methylpentanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / DIBAL-H / toluene; diethyl ether / 1.25 h / -80 °C

2.1: 70 percent / (i-Pr)2NEt; LiCl / acetonitrile / 24 h / 20 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C

4.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -80 °C

4.2: trisyl azide / tetrahydrofuran; toluene / 0.07 h / -80 °C

4.3: 68 percent / acetic acid / tetrahydrofuran; toluene / -80 - 20 °C

5.1: 99 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

6.1: 92 percent / LiOH; aq. H₂O₂ / tetrahydrofuran; H₂O / 20 h / 24 °C

7.1: 75 percent / DMAP; Boc₂O / 0.5 h / 20 °C

8.1: 37 percent / DMAP; Et₃N / dioxane / 12 h / 100 °C

With dmap; lithium hydroxide; di-tert-butyl dicarbonate; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1002/ejoc.200600154