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

Base Information

Chemical Name:(2S,3R,4E)-3-amino-1-benzyloxyoctadec-4-en-2-ol
CAS No.:511542-05-5
Molecular Formula:C₂₅H₄₃NO₂
Molecular Weight:389.622
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about (2S,3R,4E)-3-amino-1-benzyloxyoctadec-4-en-2-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: 95.0%

: 511542-11-3
(4R,5S)-5-benzyloxymethyl-4-[(E)-pentadec-1-enyl]oxazolidin-2-one

: 511542-05-5
(2S,3R,4E)-3-amino-1-benzyloxyoctadec-4-en-2-ol

Guidance literature:: With potassium hydroxide; In ethanol; water; for 3h; Heating;
DOI:10.1021/jo0268254

Reference yield:

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

: 511542-05-5
(2S,3R,4E)-3-amino-1-benzyloxyoctadec-4-en-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 2.7 g / LiOH*H₂O; 4 Angstroem molecular sieves / tetrahydrofuran / 2.5 h / Heating

2: 59 percent / DIBALH / CH₂Cl₂; hexane / 1.5 h / -40 °C

3: 95 percent / NaH; Bu₄NI / tetrahydrofuran / 48 h / Heating

4: 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: 75 percent / (dba)3Pd₂*CHCl₃; P(i-PrO)3 / tetrahydrofuran / 1.5 h / 20 °C

6: 88 percent / sodium naphthalide / tetrahydrofuran / 0.33 h / -78 °C

7: 95 percent / KOH / ethanol; H₂O / 3 h / Heating

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; Oxone; potassium hydroxide; lithium hydroxide; triisopropyl phosphite; 4 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide; sodium naphthalenide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 4,5-O-Me₂C-3-oxo-THP-2-spiro-4'-2',2'-Me₂-1',3'-dioxolan; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetonitrile; 1: Wittig reaction;
DOI:10.1021/jo0268254

Reference yield:

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

: 511542-05-5
(2S,3R,4E)-3-amino-1-benzyloxyoctadec-4-en-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 59 percent / DIBALH / CH₂Cl₂; hexane / 1.5 h / -40 °C

2: 95 percent / NaH; Bu₄NI / tetrahydrofuran / 48 h / Heating

3: 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: 75 percent / (dba)3Pd₂*CHCl₃; P(i-PrO)3 / tetrahydrofuran / 1.5 h / 20 °C

5: 88 percent / sodium naphthalide / tetrahydrofuran / 0.33 h / -78 °C

6: 95 percent / KOH / ethanol; H₂O / 3 h / Heating

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; Oxone; potassium hydroxide; triisopropyl phosphite; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide; sodium naphthalenide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 4,5-O-Me₂C-3-oxo-THP-2-spiro-4'-2',2'-Me₂-1',3'-dioxolan; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0268254