Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

Base Information

• Chemical Name: Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate
• CAS No.: 139560-99-9
• Molecular Formula: C₅₂H₅₁BrN₂O₈
• Molecular Weight: 911.89

Synonyms:Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

Chemical Property of Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

Chemical Property:

Purity/Quality:

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Technology Process of Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

There total 16 articles about Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--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:

Ethyl (Z)-2-(N-benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate (139559-29-8) → Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate (139560-99-9) + Ethyl (E)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate (139427-61-5)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; bromine; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; CH₂Cl₂, -10 deg C;

DOI:10.1021/jo00034a002

Reference yield:

2-Benzoylamino-2-(diethoxyphosphoryl)essigsaeure-ethylester (85992-73-0) → Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate (139560-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / heptane; tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 1 h, 2.) -20 deg C, overnight

2: Br₂, 2,6-lutidine / CH₂Cl₂ / 1.5 h / -10 °C

With 2,6-dimethylpyridine; bromine; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane;

DOI:10.1021/jo00079a033

Reference yield:

(2'S)-3--2(R),3(R)-bis<(p-methoxybenzyl)oxy>-1-propanal (137845-83-1) → Ethyl (Z)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate (139560-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / heptane; tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 1 h, 2.) -20 deg C, overnight

2: Br₂, 2,6-lutidine / CH₂Cl₂ / 1.5 h / -10 °C

With 2,6-dimethylpyridine; bromine; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane;

DOI:10.1021/jo00079a033

upstream raw materials:

Ethyl (E)-2-(N-Benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

Ethyl (Z)-2-(N-benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

2-Benzoylamino-2-(diethoxyphosphoryl)essigsaeure-ethylester

(2'S)-3--2(R),3(R)-bis<(p-methoxybenzyl)oxy>-1-propanal

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