N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

Base Information

Chemical Name:N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester
CAS No.:444154-81-8
Molecular Formula:C₃₁H₃₅N₃O₈
Molecular Weight:577.634
Hs Code.:

Synonyms:N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

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Chemical Property of N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

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Technology Process of N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

There total 5 articles about N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl 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: 54.0%

: β-alanyl-β-alanine methyl ester hydrochloride

: 444154-78-3
(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropioic acid

: 444154-81-8
N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

Guidance literature:: With dmap; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃;
DOI:10.1021/jo0256078

Reference yield:

: 3943-94-0,6236-62-0,17041-46-2
3-(2-hydroxy-phenyl)-acrylic acid ethyl ester

: 444154-81-8
N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.490 g / K₂CO₃ / dimethylformamide / 20 °C

2: NaOh; t-BuOCl; (DHQD)2AQN / K₂[OsO₂(OH)4] / H₂O; propan-1-ol / 2 h / 20 °C

3: 93 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

4: 54 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydroquinidine anthraquinone-1,4-diyl diether; tert-butylhypochlorite; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; K2; In tetrahydrofuran; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; 2: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/jo0256078

Reference yield:

: 495-79-4,583-17-5,614-60-8
2-hydroxycinnamic acid

: 444154-81-8
N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: conc. H₂SO₄ / 5 h / Heating

2: 1.490 g / K₂CO₃ / dimethylformamide / 20 °C

3: NaOh; t-BuOCl; (DHQD)2AQN / K₂[OsO₂(OH)4] / H₂O; propan-1-ol / 2 h / 20 °C

4: 93 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

5: 54 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydroquinidine anthraquinone-1,4-diyl diether; tert-butylhypochlorite; sulfuric acid; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; K2; In tetrahydrofuran; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; 3: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/jo0256078