Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester

Base Information

Chemical Name:Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester
CAS No.:215171-17-8
Molecular Formula:C₁₆H₂₃NO₅
Molecular Weight:309.362
Hs Code.:

Synonyms:Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester

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Chemical Property of Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester

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Technology Process of Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester

There total 5 articles about Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl 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: 83.0%

: 215171-16-7
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl ester

: 215171-17-8
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(98)00741-8

Reference yield:

: 100-58-3
phenylmagnesium bromide

: 215171-17-8
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Et₂AlCl / 1.) Et₂O, room temp., 15 min, 2.) Et₂O, -60 deg C, 6 h

2: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h

3: 100 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating

4: 92 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

5: 100 percent / pyridine / 1 h / Ambient temperature

6: 83 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; hydrogen; diethylaluminium chloride; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00741-8

Reference yield:

: 192764-07-1
N-Benzyl-N-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine

: 215171-17-8
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-1-hydroxymethyl-2-phenyl-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h

2: 100 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating

3: 92 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

4: 100 percent / pyridine / 1 h / Ambient temperature

5: 83 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00741-8