(2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester
• CAS No.: 144664-88-0
• Molecular Formula: C₂₂H₂₆N₂O₆
• Molecular Weight: 414.458

Synonyms:(2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester

Chemical Property of (2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester

Chemical Property:

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Technology Process of (2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester

There total 2 articles about (2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid 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:

(2S,3S)-methyl 2-amino-3-hydroxybutanoate (3373-59-9,53216-06-1,68331-48-6,79617-28-0,82679-55-8,118525-51-2) + N-Cbz-L-Phe (1161-13-3) → (2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester (144664-88-0)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(00)61250-9

Reference yield:

N-Cbz-L-Phe (1161-13-3) + L-threonine methyl ester hydrochloride (39994-75-7,60538-15-0,60538-18-3,62076-66-8,76419-75-5,79617-27-9,108724-12-5) → CBZ-Phe-Thr-OMe (17554-22-2,144664-88-0)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1) dioxane, 0 deg C, 15 min., 2) dioxane, 6 h;

DOI:10.1016/S0040-4039(00)74743-5

Reference yield: 87.0%

(2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester (144664-88-0) → (2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-nitrooxy-butyric acid methyl ester

Guidance literature:

With lithium nitrate; sodium carbonate; trifluoroacetic anhydride; In acetonitrile; at 0 ℃;

DOI:10.1016/j.tetlet.2005.07.065

upstream raw materials:

N-Cbz-L-Phe

L-threonine methyl ester hydrochloride

(2S,3S)-methyl 2-amino-3-hydroxybutanoate

Downstream raw materials:

(2S,3S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester

(2S,3S)-2-((S)-2-{(S)-2-[(S)-3-((2R,3R,4R,5R,6S)-3-Acetoxy-5-hydroxy-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-acetylamino-propionylamino]-3-hydroxy-propionylamino}-3-phenyl-propionylamino)-3-hydroxy-butyric acid methyl ester

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