N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

Base Information

Chemical Name:N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol
CAS No.:135042-15-8
Molecular Formula:C₂₃H₃₉NO₆SSi
Molecular Weight:485.717
Hs Code.:

Synonyms:N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

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Chemical Property of N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

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Technology Process of N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

There total 6 articles about N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol 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: 84.4%

: 135042-14-7
N-(tert-butoxycarbonyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 135042-15-8
N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 41h; Ambient temperature;
DOI:10.1021/jm00113a017

Reference yield:

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

: 135042-15-8
N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

Guidance literature:: Multi-step reaction with 5 steps

1: 82.5 percent / aq. NaOH / tetrahydrofuran / Ambient temperature

2: 92.4 percent / dioxane; diethyl ether / 0.25 h / 5 °C

3: 1.) Ph₃P, diethyl azodicarboxylate (DEAD) / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 5 h

4: LiBH₄ / 1,2-dimethoxy-ethane / 17.5 h / Ambient temperature

5: 84.4 percent / imidazole / dimethylformamide / 41 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; lithium borohydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jm00113a017

Reference yield:

: 135042-12-5,946610-68-0
(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline

: 135042-15-8
N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-trans-4-(p-toluenesulfonyloxy)-D-prolinol

Guidance literature:: Multi-step reaction with 4 steps

1: 92.4 percent / dioxane; diethyl ether / 0.25 h / 5 °C

2: 1.) Ph₃P, diethyl azodicarboxylate (DEAD) / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 5 h

3: LiBH₄ / 1,2-dimethoxy-ethane / 17.5 h / Ambient temperature

4: 84.4 percent / imidazole / dimethylformamide / 41 h / Ambient temperature

With 1H-imidazole; lithium borohydride; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; 1,2-dimethoxyethane; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jm00113a017