methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate

Base Information

• Chemical Name: methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate
• CAS No.: 1451147-95-7
• Molecular Formula: C₂₅H₄₂O₆Si
• Molecular Weight: 466.69
• Mol file: 1451147-95-7.mol

Synonyms:

Chemical Property of methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate

There total 4 articles about methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate 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: 60.0%

1,5-dimethoxy-1,4-cyclohexadiene (37567-78-5) + C19H34O4Si (1451147-96-8) → methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate (1451147-95-7)

Guidance literature:

In N,N-dimethyl-aniline; at 180 ℃; for 48h; Sealed tube;

DOI:10.1016/j.tetlet.2013.07.055

Reference yield:

2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetaldehyde (1346851-58-8) → methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate (1451147-95-7)

Guidance literature:

Multi-step reaction with 4 steps

1: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / toluene / -30 °C

2: dmap; 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C

3: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

4: N,N-dimethyl-aniline / 48 h / 180 °C / Sealed tube

With 1H-imidazole; dmap; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; n-butyllithium; In tetrahydrofuran; dichloromethane; N,N-dimethyl-aniline; toluene; 4: |Alder-Rickert Cycloaddition;

DOI:10.1016/j.tetlet.2013.07.055

Reference yield:

(R)-1-((2R,6R)-6-methyl-tetrahydro-2H-pyran-2-yl)pent-4-yn-2-ol (1451147-99-1) → methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-3-((2R,6R)-6-methyl-tetrahydro-2Hpyran-2-yl)propyl)-4,6-dimethoxybenzoate (1451147-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C

2: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

3: N,N-dimethyl-aniline / 48 h / 180 °C / Sealed tube

With 1H-imidazole; dmap; n-butyllithium; In tetrahydrofuran; dichloromethane; N,N-dimethyl-aniline; 3: |Alder-Rickert Cycloaddition;

DOI:10.1016/j.tetlet.2013.07.055

upstream raw materials:

2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetaldehyde

(R)-1-((2R,6R)-6-methyl-tetrahydro-2H-pyran-2-yl)pent-4-yn-2-ol

C₁₇H₃₂O₂Si

1,5-dimethoxy-1,4-cyclohexadiene