Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate

Base Information

• Chemical Name: Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate
• CAS No.: 134676-39-4
• Molecular Formula: C₂₆H₃₀N₂O₅
• Molecular Weight: 450.535

Synonyms:Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate

Chemical Property of Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate

Chemical Property:

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Technology Process of Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate

There total 4 articles about Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate 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: 75.0%

Benzyl (4RS)-(E)-4-Acetoxy-5-<(tert-butoxycarbonyl)amino>-2-(3-indolylmethyl)-2-pentenoate (134676-38-3) → Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate (134676-39-4)

Guidance literature:

With sodium carbonate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00006a027

Reference yield: 56.0%

Benzyl (4RS)-(E)-4-Acetoxy-5-<(tert-butoxycarbonyl)amino>-2-(3-indolylmethyl)-2-pentenoate (134676-38-3) → Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate (134676-39-4) + (E)-3-[(2R,3S)-3-(2,2-Dimethyl-propionylamino)-5-oxo-tetrahydro-furan-2-yl]-2-(1H-indol-3-ylmethyl)-acrylic acid benzyl ester + (E)-3-[(2S,3S)-3-(2,2-Dimethyl-propionylamino)-5-oxo-tetrahydro-furan-2-yl]-2-(1H-indol-3-ylmethyl)-acrylic acid benzyl ester

Guidance literature:

With sodium carbonate; In methanol; for 0.75h; Ambient temperature;

DOI:10.1016/S0040-4039(00)95477-7

Reference yield:

Acetic acid 1-(tert-butoxycarbonylamino-methyl)-allyl ester (134676-37-2) → Benzyl (4RS)-(E)-5-<(tert-Butoxycarbonyl)amino>-4-hydroxy-2-(3-indolylmethyl)-2-pentenoate (134676-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NMO, 2) NaIO₄

2: 75 percent / Na₂CO₃ / methanol / 1 h / Ambient temperature

With sodium periodate; N-methyl-2-indolinone; sodium carbonate; In methanol;

DOI:10.1021/jo00006a027

upstream raw materials:

Benzyl (4RS)-(E)-4-Acetoxy-5-<(tert-butoxycarbonyl)amino>-2-(3-indolylmethyl)-2-pentenoate

Acetic acid 1-(tert-butoxycarbonylamino-methyl)-allyl ester

3-(1H-Indol-3-yl)-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid benzyl ester

Downstream raw materials:

Benzyl (4RS)-(E)-4-Bromo-5-<(tert-butoxycarbonyl)amino>-2-(3-indolylmethyl)-2-pentenoate

Boc-Glyψ-D,L-Trp-OBn

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