(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

Base Information

Chemical Name:(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester
CAS No.:870192-69-1
Molecular Formula:C₂₅H₃₃NO₇
Molecular Weight:459.54
Hs Code.:

Synonyms:(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

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Chemical Property of (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

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Technology Process of (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

There total 1 articles about (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl 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: 95.0%

: (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-diisopropoxy-2,4-dimethyl-pentyl ester

: 870192-69-1
(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; at 25 ℃; for 12h;
DOI:10.1016/j.tetlet.2005.09.037

Reference yield: 95.0%

: 870192-69-1
(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 870192-70-4
(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3R,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 0.25h;
DOI:10.1016/j.tetlet.2005.09.037

Reference yield:

: 870192-69-1
(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester

: 845521-50-8
N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methylhexadecyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / imidazole / dimethylformamide / 0.25 h / 25 °C

2.1: 50 percent / LHMDS / tetrahydrofuran / 0.17 h / -40 °C

3.1: KBr; NaHCO₃; aq. NaClO / TEMPO / CH₂Cl₂ / 0.75 h / 0 °C

4.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

4.2: tetrahydrofuran / 0.25 h

5.1: H₂; ethylenediamine / Pd/C / methanol / 0.5 h / 25 °C

6.1: HOBt; EDCI / dimethylformamide / 0.5 h / 25 °C

7.1: 90 percent / aq. acetic acid / tetrahydrofuran / 18 h / 25 °C

With 1H-imidazole; sodium hypochlorite; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethylenediamine; potassium bromide; lithium hexamethyldisilazane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.2: Wittig reaction;
DOI:10.1016/j.tetlet.2005.09.037