(S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

Base Information

• Chemical Name: (S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol
• CAS No.: 1222190-43-3
• Molecular Formula: C₂₂H₃₄O₃
• Molecular Weight: 346.51
• Mol file: 1222190-43-3.mol

Synonyms:(S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

Chemical Property of (S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

There total 8 articles about (S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-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: 84.0%

1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one (1222190-49-9) → (R)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1222190-40-0) + (S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1222190-43-3)

Guidance literature:

With lithium aluminium tetrahydride; lithium iodide; at -100 - -40 ℃; for 0.5h;

DOI:10.1002/ejoc.201100888

Reference yield:

Octanal (124-13-0) → (R)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1222190-40-0) + (S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1222190-43-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 36 h / -15 °C / Molecular sieve

2.1: ozone / dichloromethane / 0.08 h / -78 °C

2.2: 18 h / 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C

4.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / 20 °C

5.1: lithium aluminium tetrahydride; lithium iodide / 0.5 h / -100 - -40 °C

With titanium(IV) isopropylate; lithium aluminium tetrahydride; potassium tert-butylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; ozone; magnesium; lithium iodide; In tetrahydrofuran; dichloromethane; ethylene dibromide; toluene; 1.1: Keck allylation / 2.2: Wittig-Horner reaction;

DOI:10.1002/ejoc.201100888

Reference yield:

C10H20O2 → (R)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1222190-40-0) + (S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1222190-43-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 20 °C

1.2: 18 h / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C

3.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / 20 °C

4.1: lithium aluminium tetrahydride; lithium iodide / 0.5 h / -100 - -40 °C

With lithium aluminium tetrahydride; potassium tert-butylate; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium iodide; In tetrahydrofuran; ethylene dibromide; acetonitrile; 1.1: Wittig-Horner reaction / 1.2: Wittig-Horner reaction;

DOI:10.1002/ejoc.201100888

upstream raw materials:

1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one

(R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxydecan-1-one

(R,E)-5-hydroxy-N-methoxy-N-methyldodec-2-enamide

2-((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)-N-methoxy-N-methylacetamide

Downstream raw materials:

(S,E)-6-[(2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]-5-hydroxy-N-methoxy-N-methylhex-2-enamide

2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]-N-methoxy-N-methylacetamide

2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde

ethyl (Z)-4-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]but-2-enoate