(S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane

Base Information

• Chemical Name: (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane
• CAS No.: 1609178-43-9
• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.387
• Mol file: 1609178-43-9.mol

Synonyms:(S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane

Chemical Property of (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane

There total 2 articles about (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane 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:

O,O-diethyl benzylphosphonate (1080-32-6) + (S)-2-((S)-5,5-dimethyl-4,6-dioxaspiro[2.5]octan-7-yl)propanal (1609178-42-8) → (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane (1609178-43-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.03.011

Reference yield:

2-[5,5-dimethyl-4,6-dioxaspiro[2.5]octan-7-yl]propan-1-ol → (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane (1609178-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.tetasy.2014.03.011

Reference yield: 88.0%

methanol (67-56-1) + (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane (1609178-43-9) → (3S,4R,E)-methyl 3-hydroxy-4-methyl-6-phenylhex-5-enoate (1609178-44-0)

Guidance literature:

methanol; (S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane; With pyridinium p-toluenesulfonate; for 0.333333h; Reflux;

With [bis(acetoxy)iodo]benzene; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetasy.2014.03.011

upstream raw materials:

O,O-diethyl benzylphosphonate

(S)-2-((S)-5,5-dimethyl-4,6-dioxaspiro[2.5]octan-7-yl)propanal

Downstream raw materials:

(3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate

(3S,4R,5E)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-6-phenyl-5-hexenal

(2E,5S,6R,7E)-ethyl 5-hydroxy-6-methyl-8-phenylocta-2,7-dienoate

(3S,4R,E)-methyl 3-hydroxy-4-methyl-6-phenylhex-5-enoate