N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester

Base Information

• Chemical Name: N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester
• CAS No.: 683773-05-9
• Molecular Formula: C₂₃H₂₅Cl₃N₂O₆
• Molecular Weight: 531.82

Synonyms:N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester

Chemical Property of N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester

Chemical Property:

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Technology Process of N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester

There total 3 articles about N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl 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: 79.0%

D-allothreonine benzyl ester hydrochloride + N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalanine (683773-04-8) → N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester (683773-05-9)

Guidance literature:

With 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; In dichloromethane;

DOI:10.1021/jo030304e

Reference yield:

(2R,3R)-2-Azido-3-hydroxy-butyric acid benzyl ester (176505-52-5) → N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester (683773-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / hydrogen; aq. HCl / Pt/C / dioxane / normal pressure

2: 79 percent / IIDQ / CH₂Cl₂

With hydrogenchloride; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; hydrogen; platinum on activated charcoal; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jo030304e

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester (683773-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / aq. NaOH / 20 °C

2: 79 percent / IIDQ / CH₂Cl₂

With sodium hydroxide; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; In dichloromethane;

DOI:10.1021/jo030304e

upstream raw materials:

N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalanine

D-(R)-phenylalanine

(2R,3R)-2-Azido-3-hydroxy-butyric acid benzyl ester

Downstream raw materials:

N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(2-O-chloroacetyl-3,4-O-isopropylidene-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

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