1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol

Base Information

• Chemical Name: 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol
• CAS No.: 1610613-90-5
• Molecular Formula: C₄₅H₈₂O₃
• Molecular Weight: 671.144
• Mol file: 1610613-90-5.mol

Synonyms:1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol

Chemical Property of 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol

There total 28 articles about 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol 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: 67.0%

(10R,S)-1-bromo-10-methylhexadecane (1610613-74-5) + 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-snglycerol (1610613-85-8) → 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol (1610613-90-5)

Guidance literature:

1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-snglycerol; With potassium hydride; In toluene; at 20 ℃; for 20h; Inert atmosphere;

(10R,S)-1-bromo-10-methylhexadecane; In toluene; for 12h; Reflux; Inert atmosphere;

DOI:10.1039/c4ob00048j

Reference yield:

7-bromo-hept-1-ene (4117-09-3) → 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol (1610613-90-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydride / toluene / 8 h / Reflux

2.1: potassium hydroxide / water; ethanol / 8 h / Reflux

3.1: Isopropylbenzene; pyridine / 1 h / Reflux

4.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux

5.1: pyridinium p-toluenesulfonate / dichloromethane

6.1: dibromotriphenylphosphorane / dichloromethane / 20 °C

7.1: magnesium / diethyl ether / 3 h / Reflux

7.2: 3 h / -3 - 0 °C

8.1: triphenylphosphine; bromine / dichloromethane / 0 - 20 °C

9.1: potassium hydride / toluene / 18 h / 20 °C

9.2: 10 h / Reflux

10.1: methanol; pyridinium p-toluenesulfonate / 10 h / Reflux

11.1: di(n-butyl)tin oxide / methanol; toluene / 1 h / 20 °C / Molecular sieve; Reflux

11.2: 2.5 h / Molecular sieve; Reflux

12.1: potassium hydride / toluene / 20 h / 20 °C / Inert atmosphere

12.2: 12 h / Reflux; Inert atmosphere

With pyridine; methanol; lithium aluminium tetrahydride; Isopropylbenzene; bromine; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; di(n-butyl)tin oxide; magnesium; triphenylphosphine; potassium hydroxide; dibromotriphenylphosphorane; In methanol; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1039/c4ob00048j

Reference yield:

6-bromo-4-methyl-hexanal → 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol (1610613-90-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium tetrahydroborate / methanol / 20 °C

2.1: pyridinium p-toluenesulfonate / dichloromethane / 18 h / 20 °C

3.1: magnesium / diethyl ether / 2 h / Reflux

3.2: -5 - 0 °C

4.1: triphenylphosphine; bromine / dichloromethane / 0 - 20 °C

5.1: magnesium / tetrahydrofuran

5.2: 0 °C

6.1: triphenylphosphine; bromine / dichloromethane / 0 - 20 °C

7.1: potassium hydride / toluene / 18 h / 20 °C

7.2: 10 h / Reflux

8.1: methanol; pyridinium p-toluenesulfonate / 10 h / Reflux

9.1: di(n-butyl)tin oxide / methanol; toluene / 1 h / 20 °C / Molecular sieve; Reflux

9.2: 2.5 h / Molecular sieve; Reflux

10.1: potassium hydride / toluene / 20 h / 20 °C / Inert atmosphere

10.2: 12 h / Reflux; Inert atmosphere

With methanol; sodium tetrahydroborate; bromine; pyridinium p-toluenesulfonate; potassium hydride; di(n-butyl)tin oxide; magnesium; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1039/c4ob00048j

upstream raw materials:

citronellylbromide

(2RS)-1-bromo-2-methyloctane

C₁₀H₂₂O₃S

hept-6-en-1-yl(methyl)malonic acid diethyl ester

Refernces