Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide

Base Information

• Chemical Name: Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide
• CAS No.: 761407-97-0
• Molecular Formula: C₅₈H₉₃NO₄Si
• Molecular Weight: 896.466

Synonyms:Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide

Chemical Property of Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide

Chemical Property:

Purity/Quality:

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Technology Process of Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide

There total 9 articles about Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide 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:

Benzoic acid (2S,3S)-3-azido-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-butyl ester (761408-02-0) → Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide (761407-97-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 75 percent / NaHCO₃ / La(OTf)3 / toluene / 2 h

2.1: 81 percent / NaOMe / methanol / 1 h / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

3.2: 92 percent / NaOH / CH₂Cl₂; H₂O; diethyl ether / 20 °C

4.1: 76 percent / BuLi / tetrahydrofuran / -78 - 20 °C

5.1: 83 percent / NH₄Cl; Zn / methanol / 2 h / 20 °C

6.1: 76 percent / diisopropylethylamine / toluene / 2 h / 20 °C

7.1: 82 percent / RuCl₂[(1,3-dimesitylimidazolidine-2-yl)(PCy₃)(benzylidene)] / CH₂Cl₂ / 36 h / Heating

8.1: piperidine / dimethylformamide / 0.08 h

9.1: 12 mg / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

With piperidine; dmap; n-butyllithium; sodium methylate; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lanthanum(lll) triflate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Wittig methylenation;

DOI:10.1021/ol049183a

Reference yield:

(2S,3S)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyraldehyde (761407-84-5) → Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide (761407-97-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / BuLi / tetrahydrofuran / -78 - 20 °C

2: 83 percent / NH₄Cl; Zn / methanol / 2 h / 20 °C

3: 76 percent / diisopropylethylamine / toluene / 2 h / 20 °C

4: 82 percent / RuCl₂[(1,3-dimesitylimidazolidine-2-yl)(PCy₃)(benzylidene)] / CH₂Cl₂ / 36 h / Heating

5: piperidine / dimethylformamide / 0.08 h

6: 12 mg / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

With piperidine; dmap; n-butyllithium; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Wittig methylenation;

DOI:10.1021/ol049183a

Reference yield:

(2S,3S)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butan-1-ol (761408-03-1) → Hexadecanoic acid [(E)-(1S,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl]-amide (761407-97-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

1.2: 92 percent / NaOH / CH₂Cl₂; H₂O; diethyl ether / 20 °C

2.1: 76 percent / BuLi / tetrahydrofuran / -78 - 20 °C

3.1: 83 percent / NH₄Cl; Zn / methanol / 2 h / 20 °C

4.1: 76 percent / diisopropylethylamine / toluene / 2 h / 20 °C

5.1: 82 percent / RuCl₂[(1,3-dimesitylimidazolidine-2-yl)(PCy₃)(benzylidene)] / CH₂Cl₂ / 36 h / Heating

6.1: piperidine / dimethylformamide / 0.08 h

7.1: 12 mg / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

With piperidine; dmap; n-butyllithium; ammonium chloride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: Wittig methylenation;

DOI:10.1021/ol049183a

upstream raw materials:

n-hexadecanoyl chloride

(2S,3S)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyraldehyde

Benzoic acid (2S,3S)-3-azido-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-butyl ester

(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-but-3-enylamine

Downstream raw materials:

1-OTBDPS ceramide

(2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol

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