benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate

Base Information

• Chemical Name: benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate
• CAS No.: 1327254-69-2
• Molecular Formula: C₄₄H₇₈O₅Si
• Molecular Weight: 715.186
• Mol file: 1327254-69-2.mol

Synonyms:benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate

Chemical Property of benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate

There total 9 articles about benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate 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%

[11-(benzyloxy)-11-oxoundecyl]triphenylphosphonium bromide (1127645-17-3) + C26H52O4Si (1327254-75-0) → benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate (1327254-69-2)

Guidance literature:

[11-(benzyloxy)-11-oxoundecyl]triphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 0 ℃; for 1h;

C₂₆H₅₂O₄Si; In tetrahydrofuran; toluene; at -78 - 20 ℃;

DOI:10.1016/j.tet.2011.06.023

Reference yield:

methyl (R)-5-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((triethylsilyl)oxy)pentanoate (1327254-65-8) → benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate (1327254-69-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 - 0 °C

2.2: -78 - 20 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 2.2: Wittig reaction;

DOI:10.1016/j.tet.2011.06.023

Reference yield:

methyl (R)-5-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypentanoate (1327254-64-7) → benzyl (R,Z)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadec-11-enoate (1327254-69-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C

3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 - 0 °C

3.2: -78 - 20 °C

With dmap; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.2: Wittig reaction;

DOI:10.1016/j.tet.2011.06.023

upstream raw materials:

[11-(benzyloxy)-11-oxoundecyl]triphenylphosphonium bromide

C₂₆H₅₂O₄Si

methyl (R)-5-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypentanoate

methyl (R)-5-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((triethylsilyl)oxy)pentanoate

Downstream raw materials:

(14S,17S,18S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-14,17,18-trihydroxyoctacosanamide

(S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-((triethylsilyl)oxy)hexadecanamide