1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-phenyl-, (4R,5S)-

Base Information

• Chemical Name: 1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-phenyl-, (4R,5S)-
• CAS No.: 155749-26-1
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• DSSTox Substance ID: DTXSID00448064
• Nikkaji Number: J2.015.350D
• Mol file: 155749-26-1.mol

Synonyms:155749-26-1;1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-phenyl-, (4R,5S)-;DTXSID00448064;(4R,5S)-2,2-Dimethyl-5-phenyl-1,3-dioxolane-4-methanol

Chemical Property of 1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-phenyl-, (4R,5S)-

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 209

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)C2=CC=CC=C2)CO)C
• Isomeric SMILES: CC1(O[C@@H]([C@@H](O1)C2=CC=CC=C2)CO)C

Technology Process of 1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-phenyl-, (4R,5S)-

There total 12 articles about 1,3-Dioxolane-4-methanol, 2,2-dimethyl-5-phenyl-, (4R,5S)- 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: 68.0%

(4S,5R)-2,2-dimethyl-4-phenyl-5-ethenyl[1,3]dioxolane (646995-81-5) → [(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol (155749-26-1)

Guidance literature:

(4S,5R)-2,2-dimethyl-4-phenyl-5-ethenyl[1,3]dioxolane; With ozone; In dichloromethane; at -78 - 20 ℃;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2003.10.026

Reference yield: 57.0%

(5S)-2,2-dimethyl-4-methylene-5-phenyl-1,3-dioxolane (156517-44-1) → (4S,5S)-2,2-dimethyl-4-(hydroxymethyl)-5-phenyl-1,3-dioxolane (153609-00-8) + [(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol (155749-26-1)

Guidance literature:

With sodium hydroxide; borane-THF; dihydrogen peroxide; In tetrahydrofuran; water; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)77164-4

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → [(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol (155749-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (+)-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide

1.2: triethylamine; 4-(dimethylamino)pyridine

1.3: p-toluenesulfonic acid / tetrahydrofuran; H₂O

2.1: p-toluenesulfonic acid / acetone / 20 °C

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; In tetrahydrofuran; acetone;

DOI:10.1246/bcsj.80.387

upstream raw materials:

(5S)-2,2-dimethyl-4-methylene-5-phenyl-1,3-dioxolane

(4S,5R)-2,2-dimethyl-4-phenyl-5-ethenyl[1,3]dioxolane

2,2-dimethoxy-propane

(2E)-3-phenyl-2-propen-1-ol