(S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

Base Information

• Chemical Name: (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester
• CAS No.: 109826-35-9
• Molecular Formula: C₃₀H₃₂N₂O₇
• Molecular Weight: 532.593

Synonyms:(S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

Chemical Property of (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

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Technology Process of (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

There total 1 articles about (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl 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:

N-hydroxy-5-norbornene-2,3-dicarboximide (21715-90-2) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3,54784-43-9) → (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester (109826-35-9)

Guidance literature:

With WSCD*HCl; In N,N-dimethyl-formamide; acetonitrile; at 0 ℃; for 1h;

DOI:10.1248/cpb.43.1272

Reference yield: 75.5%

(R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-aminium 2,2,2-trifluoroacetate (80143-17-5) + (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester (109826-35-9) → Benzyl-tert.-butyloxycarbonyl-O-benzyl-L-tyrosyl-D-isoglutaminat (66111-55-5)

Guidance literature:

With triethylamine; In acetonitrile; for 6h; Ambient temperature;

DOI:10.1248/cpb.29.1644

Reference yield:

(S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester (109826-35-9) → (R)-4-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propionylamino]-4-carbamoyl-butyric acid benzyl ester; compound with trifluoro-acetic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 75.5 percent / NEt₃ / acetonitrile / 6 h / Ambient temperature

2: 0.33 h / Ambient temperature

With triethylamine; In acetonitrile;

DOI:10.1248/cpb.29.1644

upstream raw materials:

N-hydroxy-5-norbornene-2,3-dicarboximide

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Downstream raw materials:

Benzyl-tert.-butyloxycarbonyl-O-benzyl-L-tyrosyl-D-isoglutaminat

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