18-(Benzyloxy)-3-methyloctadec-1-EN-3-OL

Base Information

• Chemical Name: 18-(Benzyloxy)-3-methyloctadec-1-EN-3-OL
• CAS No.: 848814-60-8
• Molecular Formula: C26H44O2
• Molecular Weight: 388.634
• DSSTox Substance ID: DTXSID80575625
• Mol file: 848814-60-8.mol

Synonyms:18-(BENZYLOXY)-3-METHYLOCTADEC-1-EN-3-OL;848814-60-8;SCHEMBL3523635;DTXSID80575625

Chemical Property of 18-(Benzyloxy)-3-methyloctadec-1-EN-3-OL

Chemical Property:

• XLogP3: 8.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 19
• Exact Mass: 388.334130642
• Heavy Atom Count: 28
• Complexity: 348

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCCCCCCCCCCCCCOCC1=CC=CC=C1)(C=C)O

Technology Process of 18-(Benzyloxy)-3-methyloctadec-1-EN-3-OL

There total 6 articles about 18-(Benzyloxy)-3-methyloctadec-1-EN-3-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: 89.0%

16-methyloctadec-17-ene-1,16-diol (918876-22-9) + benzyl bromide (100-39-0) → 18-(benzyloxy)-3-methyloctadec-1-en-3-ol (848814-60-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; Heating;

DOI:10.1016/j.tet.2006.09.082

Reference yield: 88.7%

17-benzyloxyheptadecan-2-one (848814-59-5) + vinyl magnesium bromide (1826-67-1) → 18-(benzyloxy)-3-methyloctadec-1-en-3-ol (848814-60-8)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 3h;

Reference yield:

17-(tert-butyldimethylsilyloxy)heptadecan-2-one (918876-19-4) → 18-(benzyloxy)-3-methyloctadec-1-en-3-ol (848814-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 0 - 20 °C

2: 0.35 g / tetrabutylammonium fluoride / tetrahydrofuran / 15 h

3: 89 percent / sodium hydride / tetrahydrofuran / Heating

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.09.082

upstream raw materials:

16-methyloctadec-17-ene-1,16-diol

benzyl bromide

17-(tert-butyldimethylsilyloxy)heptadecan-2-one

15-hexadecanolide

Downstream raw materials:

2-(15-(benzyloxy)pentadecyl)-6-methoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene

2-(15-(benzyloxy)pentadecyl)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl acetate

2-(15-(benzyloxy)pentadecyl)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-ol

Refernces

• 1、 Muller, Thierry,Coowar, Djalil,Hanbali, Mazen,Heuschling, Paul,Luu, Bang. "Improved synthesis of tocopherol fatty alcohols and analogs: microglial activation modulators". . p. 12025 - 12040. Retrieved 2007/10/03.