(3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester

Base Information

Chemical Name:(3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester
CAS No.:919518-32-4
Molecular Formula:C₃₃H₄₀N₂O₈
Molecular Weight:592.689
Hs Code.:

Synonyms:(3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester

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Chemical Property of (3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester

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Technology Process of (3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester

There total 6 articles about (3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl 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: 65.0%

: 911050-85-6
(2R,4S)-2-(2-tert-butoxy-2-oxoethyl)-5-methoxymethoxy-4-[(4-phenoxybenzoyl)amino]pentanoic acid

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 919518-32-4
(3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester

Guidance literature:: With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1016/j.bmc.2006.05.040

Reference yield:

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

: 919518-32-4
(3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 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: 100 percent / tetrahydrofuran / 3 h / -78 °C

4.1: 94 percent / NaOH / tetrahydrofuran; methanol; H₂O / 4 h / 20 °C

5.1: 65 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 3 h / 20 °C

With sodium hydroxide; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; water; 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

: 919518-32-4
(3R,5S)-3-Benzyloxycarbamoyl-6-methoxymethoxy-5-(4-phenoxy-benzoylamino)-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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: 100 percent / tetrahydrofuran / 3 h / -78 °C

5.1: 94 percent / NaOH / tetrahydrofuran; methanol; H₂O / 4 h / 20 °C

6.1: 65 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 3 h / 20 °C

With sodium hydroxide; 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; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.05.040