5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester

Base Information

• Chemical Name: 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester
• CAS No.: 161458-88-4
• Molecular Formula: C₁₇H₂₂BrNO₂S
• Molecular Weight: 384.337
• Mol file: 161458-88-4.mol

Synonyms:5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester

Chemical Property of 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester

There total 5 articles about 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic 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: 83.0%

benzaldehyde (100-52-7) + 5-<4(S)-Amino-3(R)-bromotetrahydrothiophen-2(R)-yl>pentanoic acid methyl ester hydrobromide → 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester (161458-88-4)

Guidance literature:

With sodium hydrogencarbonate; magnesium sulfate; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1021/jo00107a009

Reference yield:

(5-carboxypentyl)triphenylphosphonium bromide (50889-29-7) → 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester (161458-88-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / LDA / tetrahydrofuran / 1 h / Ambient temperature

2: 99 percent / diethyl ether / 0 °C

3: 65 percent / Br₂, H₂O / CHCl₃ / 0.33 h / Ambient temperature

4: 85 percent / HBr / acetic acid / 20 h

5: MgSO₄ / CH₂Cl₂

With water; hydrogen bromide; bromine; magnesium sulfate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; acetic acid;

DOI:10.1016/S0040-4039(00)79354-3

Reference yield:

5-<3(R)-Bromo-4(S)-<(methoxycarbonyl)amino>tetrahydrothiophen-2(R)-yl>pentanoic acid methyl ester (151415-03-1) → 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester (161458-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / HBr / acetic acid / 20 h

2: MgSO₄ / CH₂Cl₂

With hydrogen bromide; magnesium sulfate; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4039(00)79354-3

upstream raw materials:

benzaldehyde

(5-carboxypentyl)triphenylphosphonium bromide

5-<3(R)-Bromo-4(S)-<(methoxycarbonyl)amino>tetrahydrothiophen-2(R)-yl>pentanoic acid methyl ester

cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid

Downstream raw materials:

<2S-(2α,3β,4α)>-3-Bromotetrahydro-4-<(phenylmethyl)amino>-2-thiophenepentanoic acid methyl ester

5-[(3aS,6aR)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(4Z)-ylidene]-pentanoic acid methyl ester

biotin

<3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester