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

Base Information

Chemical Name:Ethyl (E)-2-(N-Benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate
CAS No.:139559-28-7
Molecular Formula:C₅₂H₅₂N₂O₈
Molecular Weight:832.993
Hs Code.:

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

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

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

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

There total 13 articles about Ethyl (E)-2-(N-Benzoylamino)-4(R),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: 58.0%

: 85992-73-0
2-Benzoylamino-2-(diethoxyphosphoryl)essigsaeure-ethylester

: 137845-83-1
(2'S)-3--2(R),3(R)-bis<(p-methoxybenzyl)oxy>-1-propanal

: 139559-28-7
Ethyl (E)-2-(N-Benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

: 139559-29-8
Ethyl (Z)-2-(N-benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; -78 to 0 deg C;
DOI:10.1021/jo00034a002

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 139559-28-7
Ethyl (E)-2-(N-Benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

Guidance literature:: Multi-step reaction with 12 steps

1: 76 percent / NaH / dimethylformamide / 4 h / 25 °C

2: NBS, 2,6-lutidine, H₂O / acetonitrile

3: NaBH₄ / ethanol / 2 h / 25 °C

4: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

5: 66 percent / pyridinium p-toluenesulfonate / methanol / 56 h / 50 °C

6: pyridine / CH₂Cl₂ / 0 °C

7: NaN₃ / dimethylformamide / 8 h / 50 °C

8: 76 percent / Ph₃P / toluene / 0.5 h / 40 °C

9: 64 percent / pyridine / CH₂Cl₂ / 0.25 h

10: 92 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

11: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -78 °C

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

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00079a033

Reference yield:

: 2,3-O-Bis(p-methoxybenzyl)-4,5-isopropylidene-D-arabinol

: 139559-28-7
Ethyl (E)-2-(N-Benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 66 percent / pyridinium p-toluenesulfonate / methanol / 56 h / 50 °C

3: pyridine / CH₂Cl₂ / 0 °C

4: NaN₃ / dimethylformamide / 8 h / 50 °C

5: 76 percent / Ph₃P / toluene / 0.5 h / 40 °C

6: 64 percent / pyridine / CH₂Cl₂ / 0.25 h

7: 92 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

8: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -78 °C

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

With pyridine; 1H-imidazole; sodium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00079a033