Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride

Base Information

• Chemical Name: Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride
• CAS No.: 78739-33-0
• Molecular Formula: C₂₅H₄₁NO₃*ClH
• Molecular Weight: 440.066

Synonyms:Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride

Chemical Property of Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride

Chemical Property:

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Technology Process of Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride

There total 5 articles about Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride 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:

threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ2-oxazoline (78739-31-8,161968-12-3) → Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride (78739-33-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 25 ℃; for 16h;

DOI:10.1021/jo00335a015

Reference yield:

pentadec-1-yne (765-13-9) → Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride (78739-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DIBAL-H / 2.) ether, toluene, warming from 5 to 23 deg C, 1 h

2: 1.27 g / 2 N HCl / tetrahydrofuran / 16 h / 25 °C

With hydrogenchloride; diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1021/jo00335a015

Reference yield:

4-formyl-2-phenyl-Δ2-oxazoline (78715-84-1) → Benzoic acid (E)-(2S,3S)-2-amino-3-hydroxy-octadec-4-enyl ester; hydrochloride (78739-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DIBAL-H / 2.) ether, toluene, warming from 5 to 23 deg C, 1 h

2: 1.27 g / 2 N HCl / tetrahydrofuran / 16 h / 25 °C

With hydrogenchloride; diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1021/jo00335a015

upstream raw materials:

threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline

pentadec-1-yne

4-formyl-2-phenyl-Δ²-oxazoline

benzimidic acid ethyl ester

Downstream raw materials:

threo-1-O-benzoylceramide

threo-N-acetyl-1-O-benzoylsphingosine

N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

N-oleoyl-1-O-β-D-galactosyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

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