(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

Base Information

Chemical Name:(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol
CAS No.:511542-07-7
Molecular Formula:C₂₅H₄₃NO₂
Molecular Weight:389.622
Hs Code.:

Synonyms:(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

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Chemical Property of (2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

Chemical Property:

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Technology Process of (2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

There total 8 articles about (2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol 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:

: 511542-06-6
(2R,3S)-2-benzyloxymethyl-3-[(E)-pentadec-1-enyl]aziridine

: 511542-07-7
(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

Guidance literature:: (2R,3S)-2-benzyloxymethyl-3-[(E)-pentadec-1-enyl]aziridine; With di-isopropyl azodicarboxylate; trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 1.5h;

With potassium hydroxide; In dichloromethane; water; for 0.5h; Heating;
DOI:10.1021/jo0268254

Reference yield:

: 124-25-4,511542-15-7
myristylaldehyde

: 511542-07-7
(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2.7 g / LiOH*H₂O; 4 Angstroem molecular sieves / tetrahydrofuran / 2.5 h / Heating

2.1: 59 percent / DIBALH / CH₂Cl₂; hexane / 1.5 h / -40 °C

3.1: 95 percent / NaH; Bu₄NI / tetrahydrofuran / 48 h / Heating

4.1: 25 percent / Bu₄NHSO₄; Oxone; K₂CO₃ / 4,5-O-Me₂C-3-oxo-THP-2-spiro-4'-2',2'-Me₂-1',3'-dioxolan / acetonitrile; various solvent(s); H₂O / 1.5 h

5.1: 98 percent / NH₄OH / tetrahydrofuran / 2 h / 130 °C

6.1: 80 mg / PPh₃; DIAD / tetrahydrofuran / 17 h / Heating

7.1: DIAD; TFA / CH₂Cl₂; H₂O / 1.5 h / 20 °C

7.2: 1.7 mg / KOH / CH₂Cl₂; H₂O / 0.5 h / Heating

With Oxone; lithium hydroxide; ammonium hydroxide; di-isopropyl azodicarboxylate; 4 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; 4,5-O-Me₂C-3-oxo-THP-2-spiro-4'-2',2'-Me₂-1',3'-dioxolan; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 1.1: Wittig reaction / 6.1: Mitsunobu conditions;
DOI:10.1021/jo0268254

Reference yield:

: 59451-68-2
ethyl (2E,4E)-octadeca-2,4-dienoate

: 511542-07-7
(2S,3R,4E)-2-amino-1-benzyloxyoctadec-4-en-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 59 percent / DIBALH / CH₂Cl₂; hexane / 1.5 h / -40 °C

2.1: 95 percent / NaH; Bu₄NI / tetrahydrofuran / 48 h / Heating

3.1: 25 percent / Bu₄NHSO₄; Oxone; K₂CO₃ / 4,5-O-Me₂C-3-oxo-THP-2-spiro-4'-2',2'-Me₂-1',3'-dioxolan / acetonitrile; various solvent(s); H₂O / 1.5 h

4.1: 98 percent / NH₄OH / tetrahydrofuran / 2 h / 130 °C

5.1: 80 mg / PPh₃; DIAD / tetrahydrofuran / 17 h / Heating

6.1: DIAD; TFA / CH₂Cl₂; H₂O / 1.5 h / 20 °C

6.2: 1.7 mg / KOH / CH₂Cl₂; H₂O / 0.5 h / Heating

With Oxone; ammonium hydroxide; di-isopropyl azodicarboxylate; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; 4,5-O-Me₂C-3-oxo-THP-2-spiro-4'-2',2'-Me₂-1',3'-dioxolan; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 5.1: Mitsunobu conditions;
DOI:10.1021/jo0268254