Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester
CAS No.:205491-17-4
Molecular Formula:C₃₂H₄₃NO₆SSi
Molecular Weight:597.848
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

There total 6 articles about Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester 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: 86.0%

: 98-59-9
p-toluenesulfonyl chloride

: 205491-16-3
(S)-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate

: 205491-17-4
Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Guidance literature:: With dmap; triethylamine; Ambient temperature;
DOI:10.3987/com-97-s19

Reference yield:

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

: 205491-17-4
Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / 0.5M aq.Na₂CO₃ / dioxane / Ambient temperature

2: 1.) N-hydroxysuccinimide, DCC; 2.) NaBH₄ / 1.) CH₂Cl₂, r.t., 3 h; 2.) THF, EtOH, 0 deg C, 15 min

3: p-TsOH / CH₂Cl₂ / Ambient temperature

4: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

5: imidazole / CH₂Cl₂ / Ambient temperature

6: 94 percent / PdCl₂(MeCN)2 / acetonitrile / Heating

7: 86 percent / Et₃N, DMAP / Ambient temperature

With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; sodium carbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; diethyl ether; dichloromethane; acetonitrile;
DOI:10.3987/com-97-s19

Reference yield:

: 136703-59-8
(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

: 205491-17-4
Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH / CH₂Cl₂ / Ambient temperature

2: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

3: imidazole / CH₂Cl₂ / Ambient temperature

4: 94 percent / PdCl₂(MeCN)2 / acetonitrile / Heating

5: 86 percent / Et₃N, DMAP / Ambient temperature

With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.3987/com-97-s19