(4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane

Base Information

• Chemical Name: (4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane
• CAS No.: 548483-75-6
• Molecular Formula: C₁₇H₂₄O₂
• Molecular Weight: 260.376
• Mol file: 548483-75-6.mol

Synonyms:(4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane

Chemical Property of (4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane

There total 11 articles about (4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane 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: 96.0%

2,2-dimethoxy-propane (77-76-9) + (3S,5S)-1-phenyl-7-octene-3,5-diol (548483-74-5) → (4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane (548483-75-6)

Guidance literature:

With pyridinium p-toluenesulfonate; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.06.015

Reference yield:

1-phenylhex-5-en-3-ol (60340-28-5) → (4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane (548483-75-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: macroporous acrylic resin-immobilized Candida antarctica lipase B / di-isopropyl ether / 70 h / 25 °C / Inert atmosphere; Enzymatic reaction

2.1: 1H-imidazole; dmap / dichloromethane / 18 h / 25 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 12 h / Reflux

4.1: sodium periodate / water; acetonitrile / 2 h / 0 °C / Reflux

5.1: indium(III) chloride; (R)-1,1'-Bi-2-naphthol / dichloromethane / 0.17 h / Molecular sieve; Inert atmosphere

5.2: 40 h / -78 - 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

7.1: pyridinium p-toluenesulfonate / 3 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; indium(III) chloride; sodium periodate; tetrabutyl ammonium fluoride; (R)-1,1'-Bi-2-naphthol; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; di-isopropyl ether; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/j.tetasy.2012.06.015

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → (4S,6S)-4-Allyl-2,2-dimethyl-6-phenethyl-[1,3]dioxane (548483-75-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ammonium chloride; zinc / tetrahydrofuran; water / 0 - 25 °C

2.1: macroporous acrylic resin-immobilized Candida antarctica lipase B / di-isopropyl ether / 70 h / 25 °C / Inert atmosphere; Enzymatic reaction

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / Inert atmosphere

4.1: potassium hydroxide / ethanol / 8 h / 25 °C / Inert atmosphere

5.1: 1H-imidazole; dmap / dichloromethane / 18 h / 25 °C / Inert atmosphere

6.1: 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 12 h / Reflux

7.1: sodium periodate / water; acetonitrile / 2 h / 0 °C / Reflux

8.1: indium(III) chloride; (R)-1,1'-Bi-2-naphthol / dichloromethane / 0.17 h / Molecular sieve; Inert atmosphere

8.2: 40 h / -78 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

10.1: pyridinium p-toluenesulfonate / 3 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; indium(III) chloride; sodium periodate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; (R)-1,1'-Bi-2-naphthol; pyridinium p-toluenesulfonate; ammonium chloride; 4-methylmorpholine N-oxide; triphenylphosphine; potassium hydroxide; zinc; In tetrahydrofuran; ethanol; dichloromethane; di-isopropyl ether; water; acetonitrile; tert-butyl alcohol; 1.1: |Barbier Coupling Reaction / 3.1: |Mitsunobu Displacement;

DOI:10.1016/j.tetasy.2012.06.015

upstream raw materials:

2,2-dimethoxy-propane

(3S,5S)-1-phenyl-7-octene-3,5-diol

1-phenylhex-5-en-3-ol

(S)-3-acetoxy-1-phenylhex-5-ene

Downstream raw materials:

(E)-4-((4S,6S)-2,2-Dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-but-2-enal

(R)-6-[(E)-3-((4S,6S)-2,2-Dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-propenyl]-5,6-dihydro-pyran-2-one

(E)-(R)-7-((4S,6S)-2,2-Dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-hepta-1,5-dien-4-ol

acrylic acid (E)-(R)-1-allyl-4-{(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl}-but-2-enyl ester