(2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol

Base Information

• Chemical Name: (2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol
• CAS No.: 1276621-96-5
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.371
• Mol file: 1276621-96-5.mol

Synonyms:(2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol

Chemical Property of (2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol

There total 1 articles about (2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-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: 92.0%

(S)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-3-yn-2-ol (914638-76-9) + iodobenzene (591-50-4) → (2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol (1276621-96-5)

Guidance literature:

iodobenzene; With copper(l) iodide; palladium 10% on activated carbon; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 20 ℃; for 0.5h; Inert atmosphere;

(S)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-3-yn-2-ol; In 1,2-dimethoxyethane; water; at 85 ℃; for 5h; Inert atmosphere;

DOI:10.1002/cjoc.201190015

Reference yield: 86.0%

(2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol (1276621-96-5) → (2S,3E)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-buten-2-ol (1220994-32-0)

Guidance literature:

(2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

With water; sodium sulfate; In tetrahydrofuran; at 0 ℃;

DOI:10.1002/cjoc.201190015

Reference yield:

(2S)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-butyn-2-ol (1276621-96-5) → (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane (1220994-31-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 0 °C

2.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

2.2: 6.17 h / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 1 h / Inert atmosphere

5.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/cjoc.201190015

upstream raw materials:

(S)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-3-yn-2-ol

iodobenzene

Downstream raw materials:

(2S,3E)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-buten-2-ol

(2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]-1,4-dioxaspiro[4.5]decane

(2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane

(2S,4S,5E)-4-(benzyloxy)-6-phenylhex-5-ene-1,2-diol