2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 866957-63-3
• Molecular Formula: C₆₈H₁₁₇NO₁₃
• Molecular Weight: 1156.68

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester

There total 15 articles about 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester 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: 72.0%

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-pent-4-enyloxy]-tetrahydro-pyran-4-yl ester (866957-62-2) + 1-pentadecene (13360-61-7) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester (866957-63-3)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 24h; Heating;

DOI:10.1021/jo051069y

Reference yield:

Methanesulfonic acid (1R,2R)-2-hydroxy-1-hydroxymethyl-but-3-enyl ester (631090-32-9) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester (866957-63-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: imidazole / tetrahydrofuran / 0.5 h / 20 °C

2.1: 1.76 g / La(OTf)3 / toluene / 1 h / 20 °C

3.1: NaN₃; Bu₄NCl / dimethylformamide / 24 h / 90 °C

3.2: 300 mg / Et₃N; DMAP / CH₂Cl₂

4.1: 83 percent / Zn; NH₄Cl / methanol

5.1: 76 percent / Hunig's base / CH₂Cl₂

6.1: 88 percent / HF*pyridine / acetonitrile / 10 h / 20 °C

7.1: 71 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

8.1: piperidine / dimethylformamide / 0.08 h

9.1: 7.1 mg / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

10.1: 72 percent / Grubbs second-generation ruthenium carbene catalyst / CH₂Cl₂ / 24 h / Heating

With piperidine; 1H-imidazole; dmap; sodium azide; boron trifluoride diethyl etherate; tetrabutyl-ammonium chloride; ammonium chloride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; lanthanum(lll) triflate; 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; acetonitrile;

DOI:10.1021/jo051069y

Reference yield:

Methanesulfonic acid (1R,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-but-3-enyl ester → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-octadec-4-enyloxy]-tetrahydro-pyran-4-yl ester (866957-63-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1.76 g / La(OTf)3 / toluene / 1 h / 20 °C

2.1: NaN₃; Bu₄NCl / dimethylformamide / 24 h / 90 °C

2.2: 300 mg / Et₃N; DMAP / CH₂Cl₂

3.1: 83 percent / Zn; NH₄Cl / methanol

4.1: 76 percent / Hunig's base / CH₂Cl₂

5.1: 88 percent / HF*pyridine / acetonitrile / 10 h / 20 °C

6.1: 71 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

7.1: piperidine / dimethylformamide / 0.08 h

8.1: 7.1 mg / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

9.1: 72 percent / Grubbs second-generation ruthenium carbene catalyst / CH₂Cl₂ / 24 h / Heating

With piperidine; dmap; sodium azide; boron trifluoride diethyl etherate; tetrabutyl-ammonium chloride; ammonium chloride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; lanthanum(lll) triflate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo051069y

upstream raw materials:

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(2S,3R)-2-hexadecanoylamino-3-(4-methoxy-benzyloxy)-pent-4-enyloxy]-tetrahydro-pyran-4-yl ester

1-pentadecene

n-hexadecanoyl chloride

Methanesulfonic acid (1R,2R)-2-hydroxy-1-hydroxymethyl-but-3-enyl ester

Downstream raw materials:

(2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene

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