2-Propanol, 1-(hexadecyloxy)-3-(4-methoxyphenoxy)-, (2R)-

Base Information

• Chemical Name: 2-Propanol, 1-(hexadecyloxy)-3-(4-methoxyphenoxy)-, (2R)-
• CAS No.: 156737-65-4
• Molecular Formula: C26H46O4
• Molecular Weight: 422.649
• DSSTox Substance ID: DTXSID10439120
• Nikkaji Number: J1.001.235J
• Wikidata: Q82255011
• Mol file: 156737-65-4.mol

Synonyms:156737-65-4;2-Propanol, 1-(hexadecyloxy)-3-(4-methoxyphenoxy)-, (2R)-;SCHEMBL7171686;DTXSID10439120;(R)-1-(Hexadecyloxy)-3-(4-methoxyphenoxy)propane-2-ol

Chemical Property of 2-Propanol, 1-(hexadecyloxy)-3-(4-methoxyphenoxy)-, (2R)-

Chemical Property:

• XLogP3: 8.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 21
• Exact Mass: 422.33960994
• Heavy Atom Count: 30
• Complexity: 342

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCOCC(COC1=CC=C(C=C1)OC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCOC[C@H](COC1=CC=C(C=C1)OC)O

Technology Process of 2-Propanol, 1-(hexadecyloxy)-3-(4-methoxyphenoxy)-, (2R)-

There total 8 articles about 2-Propanol, 1-(hexadecyloxy)-3-(4-methoxyphenoxy)-, (2R)- 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: 50.0%

1-Hexadecanol (36653-82-4,124-29-8) + 4-methoxybenzyloxy ester of (S)-glycidol (2211-94-1,51469-79-5,71048-65-2,71031-04-4,26744-15-0) → 1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol (156737-65-4)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo980471s

Reference yield:

allyl (4-methoxyphenyl) ether (13391-35-0) → 1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol (156737-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1: AD-mix-α / 2-methyl-propan-2-ol; H2O

2: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 2.) DMF, RT

With AD-mix-α; di(n-butyl)tin oxide; cesium fluoride; In water; tert-butyl alcohol;

DOI:10.1021/jm960164j

Reference yield:

(R)-3-(p-methoxyphenoxy)-1,2-propanediol (17131-52-1,124933-35-3,131064-88-5,131064-87-4) → 1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol (156737-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / SOCl₂, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 98 percent / NaIO₄, RuCl₃*H₂O / acetonitrile; H₂O / 0.33 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min. 2.) THF, room temperature

With pyridine; ruthenium trichloride; sodium periodate; n-butyllithium; thionyl chloride; In dichloromethane; water; acetonitrile;

DOI:10.1021/jo980471s

upstream raw materials:

(R)-3-(p-methoxyphenoxy)-1,2-propanediol

hexadecanyl bromide

1-Hexadecanol

4-methoxybenzyloxy ester of (S)-glycidol

Downstream raw materials:

1-O-Hexadecyl-2-O-methyl-3-O-(4-methoxyphenyl)-sn-glycerol

1-O-hexadecyl-2-O-methyl-sn-glycerol

(2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran

(2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran