Spiro[3,6-dioxabicyclo[3.1.0]hexane-2,5-[1,3]dioxane], 2,2-dimethyl-

Base Information

• Chemical Name: Spiro[3,6-dioxabicyclo[3.1.0]hexane-2,5-[1,3]dioxane], 2,2-dimethyl-
• CAS No.: 918952-57-5
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.208
• Mol file: 918952-57-5.mol

Synonyms:Spiro[3,6-dioxabicyclo[3.1.0]hexane-2,5'-[1,3]dioxane],2',2'-dimethyl;

Chemical Property of Spiro[3,6-dioxabicyclo[3.1.0]hexane-2,5-[1,3]dioxane], 2,2-dimethyl-

Chemical Property:

• PSA: 40.22000
• LogP: 0.30570

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Spiro[3,6-dioxabicyclo[3.1.0]hexane-2,5-[1,3]dioxane], 2,2-dimethyl-

There total 6 articles about Spiro[3,6-dioxabicyclo[3.1.0]hexane-2,5-[1,3]dioxane], 2,2-dimethyl- 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: 94.0%

5-(2RS,3RS)-(3-(hydroxymethyl)oxiran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ol → (1RS,5RS)-2',2'-dimethyl-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,5'-[1',3']dioxane] (918952-57-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20 ℃; for 1.5h;

DOI:10.1021/ol062491j

Reference yield:

5-(3-hydroxyprop-1-ynyl)-2,2-dimethyl-1,3-dioxan-5-ol (918952-51-9) → (1RS,5RS)-2',2'-dimethyl-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,5'-[1',3']dioxane] (918952-57-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / quinoline; H₂ / Pd/BaSO₄ / ethanol / 7 h / 20 °C

2: imidazole / CH₂Cl₂ / 1 h / 20 °C

3: 2.41 g / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

4: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5: 94 percent / PPh₃; DEAD / toluene; tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; quinoline; tetrabutyl ammonium fluoride; hydrogen; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; Pd-BaSO₄; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/ol062491j

Reference yield:

2,2,-dimethyl-1,3-dioxan-5-one (74181-34-3) → (1RS,5RS)-2',2'-dimethyl-3,6-dioxaspiro[bicyclo[3.1.0]hexane-2,5'-[1',3']dioxane] (918952-57-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butylmagnesium chloride / tetrahydrofuran / 1.33 h / cooling

1.2: anhydrous cerium (III) chloride / tetrahydrofuran / 1.5 h / 0 °C

1.3: 84 percent / tetrahydrofuran / 1.5 h / 0 °C

2.1: 91 percent / quinoline; H₂ / Pd/BaSO₄ / ethanol / 7 h / 20 °C

3.1: imidazole / CH₂Cl₂ / 1 h / 20 °C

4.1: 2.41 g / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

6.1: 94 percent / PPh₃; DEAD / toluene; tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; quinoline; tetrabutyl ammonium fluoride; hydrogen; butyl magnesium bromide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; Pd-BaSO₄; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/ol062491j

upstream raw materials:

5-((Z)-3-Hydroxy-propenyl)-2,2-dimethyl-[1,3]dioxan-5-ol

5-(3-hydroxyprop-1-ynyl)-2,2-dimethyl-1,3-dioxan-5-ol

2,2,-dimethyl-1,3-dioxan-5-one