(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

Base Information

• Chemical Name: (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
• CAS No.: 207679-33-2
• Molecular Formula: C₃₅H₃₅BrN₂O₉
• Molecular Weight: 707.575
• Mol file: 207679-33-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 17 articles about (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 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:

p-Methoxybenzyl bromide (2746-25-0) → (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 (207679-33-2)

Guidance literature:

Multi-step reaction with 14 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

With 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; 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;

DOI:10.1021/ja992274w

Reference yield:

(3R,4R)-4-(methoxymethoxy)hexa-1,5-dien-3-ol (112531-79-0) → (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 (207679-33-2)

Guidance literature:

Multi-step reaction with 15 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

12.1: H₂ / Pd/C

14.1: N-bromosuccinimide / 25 °C

15.1: 2,2,6,6-tetramethylpiperidine / 25 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; N-Bromosuccinimide; sodium azide; L-(+)-diisopropyl tartrate; potassium tert-butylate; water; hydrogen; sodium hydride; ammonium chloride; ozone; triethylamine; triphenylphosphine; palladium on activated charcoal; 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 / 12.1: Hydrogenolysis / 13.1: Acylation / 14.1: Bromination / 15.1: tautomerization;

DOI:10.1021/ja992274w

Reference yield:

(1S,2R)-2-(methoxymethoxy)-1-((R)-oxiran-2-yl)but-3-en-1-ol (207679-21-8) → (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 (207679-33-2)

Guidance literature:

Multi-step reaction with 14 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

With 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; 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;

DOI:10.1021/ja992274w

upstream raw materials:

p-Methoxybenzyl bromide

Fmoc-OBT

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

(1S,2R)-2-(methoxymethoxy)-1-((R)-oxiran-2-yl)but-3-en-1-ol

Downstream raw materials:

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

Refernces