methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

Base Information

Chemical Name:methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate
CAS No.:911050-70-9
Molecular Formula:C₂₁H₂₅NO₇
Molecular Weight:403.432
Hs Code.:

Synonyms:methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

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Chemical Property of methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

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Technology Process of methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

There total 4 articles about methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate 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: 52.0%

: 911050-45-8
methyl (4S)-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

: 911050-70-9
methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

Guidance literature:: methyl (4S)-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

With 2-sulfonyl oxaziridine; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1016/j.bmc.2006.05.040

Reference yield:

: 911050-44-7
methyl (4S)-4-[(benzyloxy)carbonyl]amino-5-(methoxymethoxy)pentanoate

: 911050-70-9
methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogen / Pd/C / methanol / 1 h

2.1: 4.47 g / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 3 h / 20 °C

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: 52 percent / 2-sulfonyl oxaziridine / tetrahydrofuran / 3 h / -78 °C

With hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.05.040

Reference yield:

: 119109-58-9
4-(S)-[4-(N-benzyloxycarbonylamino)-5-hydroxy]pentanoic acid methyl ester

: 911050-70-9
methyl (2S,4S)-2-hydroxy-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 77 percent / ethyldiisopropylamine / CH₂Cl₂ / 2 h / 20 °C

2.1: hydrogen / Pd/C / methanol / 1 h

3.1: 4.47 g / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 3 h / 20 °C

4.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

4.2: 52 percent / 2-sulfonyl oxaziridine / tetrahydrofuran / 3 h / -78 °C

With hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.05.040