Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide

Base Information

• Chemical Name: Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide
• CAS No.: 151415-06-4
• Molecular Formula: C₁₈H₂₂N₄O₃S
• Molecular Weight: 374.464

Synonyms:Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide

Chemical Property of Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide

Chemical Property:

Purity/Quality:

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Technology Process of Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide

There total 10 articles about Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide 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: 95.0%

N-(Phenylmethyl)-3(R)-bromo-2(R)-(carbomethoxybutyl)tetrahydrothiophene-4(S)-carbamoyl azide (151415-05-3) → Δ2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide (151415-06-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 12h; Heating;

DOI:10.1016/S0040-4039(00)79354-3 DOI:10.1021/jo00107a009

Reference yield:

<2S-(2α,3β,4α)>-3-Bromotetrahydro-4-<(phenylmethyl)amino>-2-thiophenepentanoic acid methyl ester (161458-89-5) → Δ2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide (151415-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1: DBU / CH₂Cl₂ / 14 h / 0 °C

2: NaN₃ / acetone; H₂O / 12 h / Ambient temperature

3: 95 percent / DBU / tetrahydrofuran / 12 h / Heating

With sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/jo00107a009

Reference yield:

5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester (161458-88-4) → Δ2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide (151415-06-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / NaCNBH₃, buffer: citric acid pH 4 / tetrahydrofuran / 0.33 h / 0 °C

2: DBU / CH₂Cl₂ / 14 h / 0 °C

3: NaN₃ / acetone; H₂O / 12 h / Ambient temperature

4: 95 percent / DBU / tetrahydrofuran / 12 h / Heating

With sodium azide; buffer: citric acid pH 4; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/jo00107a009

upstream raw materials:

N-(Phenylmethyl)-3(R)-bromo-2(R)-(carbomethoxybutyl)tetrahydrothiophene-4(S)-carbamoyl azide

benzaldehyde

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

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

Downstream raw materials:

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

biotin

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

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

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