(S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Base Information

Chemical Name:(S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester
CAS No.:867039-07-4
Molecular Formula:C₃₃H₅₇NO₅
Molecular Weight:547.819
Hs Code.:

Synonyms:(S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

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Chemical Property of (S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

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Technology Process of (S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

There total 13 articles about (S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl 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:

: 20806-42-2
(R)-N-benzyloxycarbonyl-O-benzyl serine

: 467224-46-0
(2S,3R)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol

: 867039-07-4
(S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Guidance literature:: (R)-N-benzyloxycarbonyl-O-benzyl serine; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 ℃; for 1.5h;

(2S,3R)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol; With dmap; In tetrahydrofuran; toluene; at 0 - 25 ℃;

With hydrogen; palladium on activated charcoal; ethylenediamine; In methanol; at 25 ℃; for 0.5h;
DOI:10.1021/jo050625l

Reference yield:

: {3-[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-pentadecyl]-oxiranyl}-methanol

: 867039-07-4
(S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: CuI / tetrahydrofuran / 0 °C

1.2: 88 percent / tetrahydrofuran / 4 h / 0 °C

2.1: camphorsulfonic acid / dimethylformamide / 2 h / 0 °C

3.1: 900 mg / tetrabutylammonium fluoride / tetrahydrofuran / 96 h / 25 °C

4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

4.2: 4-dimethylaminopyridine / toluene; tetrahydrofuran / 0 - 25 °C

4.3: H₂ / Pd/C-ethylenediamine complex / methanol / 0.5 h / 25 °C

With copper(l) iodide; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo050625l

Reference yield:

: 867039-06-3
tert-Butyl-dimethyl-{(R)-1-[(R)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyloxy}-silane

: 867039-07-4
(S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 900 mg / tetrabutylammonium fluoride / tetrahydrofuran / 96 h / 25 °C

2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

2.2: 4-dimethylaminopyridine / toluene; tetrahydrofuran / 0 - 25 °C

2.3: H₂ / Pd/C-ethylenediamine complex / methanol / 0.5 h / 25 °C

With 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran;
DOI:10.1021/jo050625l