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

Base Information

• Chemical Name: (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester
• CAS No.: 207679-30-9
• Molecular Formula: C₂₈H₃₂N₂O₉
• Molecular Weight: 540.57
• Mol file: 207679-30-9.mol

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

Chemical Property of (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

There total 12 articles about (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl 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: 67.0%

methyl 2-acetylamino-2-(dimethoxyphosphinyl)acetate (89524-99-2) + (S)-2-[(1R,2S)-2-Acetoxy-1-(4-methoxy-benzyloxy)-3-oxo-propyl]-aziridine-1-carboxylic acid benzyl ester (207679-29-6) → (S)-2-[(E)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester + (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (207679-30-9)

Guidance literature:

With potassium tert-butylate; at -65 ℃;

DOI:10.1021/ja992274w

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (207679-30-9)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; hydrogenchloride; methanol; sodium azide; potassium tert-butylate; water; sodium hydride; ammonium chloride; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; 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;

DOI:10.1021/ja992274w

Reference yield:

(3R,4R)-4-(methoxymethoxy)hexa-1,5-dien-3-ol (112531-79-0) → (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (207679-30-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 90 percent / L-(+)-DIPT; t-BuOOH; Ti(O-i-Pr)4 / -10 °C

2.1: 84 percent / NaH

3.1: 74 percent / NaN₃; aq. NH₄Cl / 2-methoxy-ethanol

4.1: Ph₃P; H₂O / toluene

5.1: Et₃N

6.1: 96 percent / Et₃N

7.1: 74 percent / HCl; MeOH

8.1: 99 percent / pyridine

9.1: 100 percent / KO-t-Bu / tetrahydrofuran / -50 °C

10.1: O₃

10.2: (CH₃)2S

11.1: 67 percent / KO-t-Bu / -65 °C

With pyridine; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; sodium azide; L-(+)-diisopropyl tartrate; potassium tert-butylate; water; sodium hydride; ammonium chloride; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; 2-methoxy-ethanol; toluene; 1.1: asymmetric epoxidation / 2.1: Alkylation / 3.1: Addition / 4.1: Reduction / 5.1: N-acylation / 6.1: mesylation / 7.1: methanolysis / 8.1: Acetylation / 9.1: Cyclization / 10.1: ozonization / 10.2: Reduction / 11.1: olefination;

DOI:10.1021/ja992274w

upstream raw materials:

methyl 2-acetylamino-2-(dimethoxyphosphinyl)acetate

(S)-2-[(1R,2S)-2-Acetoxy-1-(4-methoxy-benzyloxy)-3-oxo-propyl]-aziridine-1-carboxylic acid benzyl ester

p-Methoxybenzyl bromide

(3R,4R)-4-(methoxymethoxy)hexa-1,5-dien-3-ol

Downstream raw materials:

methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate

(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

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

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