(R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol

Base Information

• Chemical Name: (R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol
• CAS No.: 164106-95-0
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317
• Mol file: 164106-95-0.mol

Synonyms:(R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol

Chemical Property of (R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol

There total 12 articles about (R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol 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: 38.0%

(4R,5R)-2,2-dimethyl-4-(2-furoyl)-5-phenyl-1,3-dioxolane (221108-29-8) → (1S,2R,3R)-1-(2-furyl)-2,3-isopropylidenyloxy-3-phenyl-1-propanol (162600-01-3) + (R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol (164106-95-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃;

Reference yield: 2.4%

furan (110-00-9) + (4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde (130718-77-3) → (1S,2R,3R)-1-(2-furyl)-2,3-isopropylidenyloxy-3-phenyl-1-propanol (162600-01-3) + (R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol (164106-95-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - -40 ℃; for 2h;

DOI:10.1016/0040-4020(94)01025-U

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (R)-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-furan-2-yl-methanol (164106-95-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / 4 Angstroem mol. sieves, (L)+diisopropyl tartarate, Ti(i-PrO)4, t-BuOOH / CH₂Cl₂ / 1 h / -15 - -5 °C

2: 90 percent / CHCl₃ / 3 h / -20 - 0 °C

3: 94 percent / imidazole / tetrahydrofuran / 24 h / Ambient temperature

4: 83 percent / K₂CO₃ / H₂O; methanol / 2 h / Ambient temperature

5: 91 percent / p-TsOH / CH₂Cl₂ / 12 h / Ambient temperature

6: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 - -20 °C

8: 2.4 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - -40 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;

DOI:10.1016/0040-4020(94)01025-U

upstream raw materials:

furan

(4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde

2-lithiofuran

(4R,5R)-2,2-dimethyl-4-(2-furoyl)-5-phenyl-1,3-dioxolane

Downstream raw materials:

(4R,5R)-2,2-dimethyl-4-(2-furoyl)-5-phenyl-1,3-dioxolane