(E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester
CAS No.:208396-50-3
Molecular Formula:C₂₀H₂₅BrN₂O₇
Molecular Weight:485.332
Hs Code.:

Synonyms:(E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

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Chemical Property of (E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

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Technology Process of (E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

There total 19 articles about (E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl 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:

: 207679-30-9
(S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

: 208396-50-3
(E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Pd/C

3: N-bromosuccinimide / 25 °C

4: 2,2,6,6-tetramethylpiperidine / 25 °C

5: piperidine / CHCl₃ / 25 °C

With piperidine; 2,2,6,6-tetramethyl-piperidine; N-Bromosuccinimide; hydrogen; palladium on activated charcoal; In chloroform; 1: Hydrogenolysis / 2: Acylation / 3: Bromination / 4: tautomerization / 5: aminolysis;
DOI:10.1021/ja992274w

Reference yield:

: 207679-33-2
(S)-2-[(E)-(1R,2S)-2-Acetoxy-4-acetylamino-3-bromo-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

: 208396-50-3
(E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

Guidance literature:: With piperidine; In chloroform; at 25 ℃;
DOI:10.1021/ja992274w

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 208396-50-3
(E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 84 percent / NaH

2.1: 74 percent / NaN₃; aq. NH₄Cl / 2-methoxy-ethanol

3.1: Ph₃P; H₂O / toluene

4.1: Et₃N

5.1: 96 percent / Et₃N

6.1: 74 percent / HCl; MeOH

7.1: 99 percent / pyridine

8.1: 100 percent / KO-t-Bu / tetrahydrofuran / -50 °C

9.1: O₃

9.2: (CH₃)2S

10.1: 67 percent / KO-t-Bu / -65 °C

11.1: H₂ / Pd/C

13.1: N-bromosuccinimide / 25 °C

14.1: 2,2,6,6-tetramethylpiperidine / 25 °C

15.1: piperidine / CHCl₃ / 25 °C

With piperidine; pyridine; 2,2,6,6-tetramethyl-piperidine; hydrogenchloride; methanol; N-Bromosuccinimide; sodium azide; potassium tert-butylate; water; hydrogen; sodium hydride; ammonium chloride; ozone; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; chloroform; 2-methoxy-ethanol; toluene; 1.1: Alkylation / 2.1: Addition / 3.1: Reduction / 4.1: N-acylation / 5.1: mesylation / 6.1: methanolysis / 7.1: Acetylation / 8.1: Cyclization / 9.1: ozonization / 9.2: Reduction / 10.1: olefination / 11.1: Hydrogenolysis / 12.1: Acylation / 13.1: Bromination / 14.1: tautomerization / 15.1: aminolysis;
DOI:10.1021/ja992274w