2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane

Base Information

• Chemical Name: 2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane
• CAS No.: 934279-86-4
• Molecular Formula: C₂₆H₃₄O₄Si
• Molecular Weight: 438.639
• Mol file: 934279-86-4.mol

Synonyms:

Chemical Property of 2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane

There total 6 articles about 2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane 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:

2-methyl-3-benzyloxy-4-benzyloxymethyl-5-methoxy-1,6-heptadiene (934279-74-0) → 2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane (934279-86-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / Grubbs' second-generation catalyst / benzene / 48 h / Heating

2: 85 percent / ammonia; sodium / tetrahydrofuran / 0.75 h / -78 °C

3: 94 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

4: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5: 55 percent / p-toluenesulfonic acid / benzene / 24 h / Heating

With 1H-imidazole; ammonia; sodium; Dess-Martin periodane; toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/j.tet.2007.01.037

Reference yield:

3-benzyloxy-4-benzyloxymethyl-5-methoxy-2-methyl-hept-6-ene-2-ol (934279-81-9) → 2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane (934279-86-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / triethylamine; MsCl / N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

2: 89 percent / Grubbs' second-generation catalyst / benzene / 48 h / Heating

3: 85 percent / ammonia; sodium / tetrahydrofuran / 0.75 h / -78 °C

4: 94 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

5: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6: 55 percent / p-toluenesulfonic acid / benzene / 24 h / Heating

With 1H-imidazole; ammonia; sodium; Dess-Martin periodane; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; In tetrahydrofuran; dichloromethane; benzene; 1: Hoffman elimination;

DOI:10.1016/j.tet.2007.01.037

Reference yield:

3-benzyloxy-4-benzyloxymethyl-2-methyl-hept-6-ene-2,5-diol (934279-80-8) → 2-methyl-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-cyclopentadien-1-[1,3]dioxolane (934279-86-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / various solvent(s); dimethylformamide / 0.5 h / 0 °C

1.2: 89 percent / various solvent(s); dimethylformamide / 1 h / 20 °C

2.1: 78 percent / triethylamine; MsCl / N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

3.1: 89 percent / Grubbs' second-generation catalyst / benzene / 48 h / Heating

4.1: 85 percent / ammonia; sodium / tetrahydrofuran / 0.75 h / -78 °C

5.1: 94 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

6.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: 55 percent / p-toluenesulfonic acid / benzene / 24 h / Heating

With 1H-imidazole; ammonia; sodium; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 2.1: Hoffman elimination;

DOI:10.1016/j.tet.2007.01.037

upstream raw materials:

4-methyl-3-hydroxy-2-hydroxymethyl-1-methoxy-4-cyclopentadiene

4-methyl-3-benzyloxy-2-benzyloxymethyl-1-methoxy-4-cyclopentadiene

2-methyl-3-benzyloxy-4-benzyloxymethyl-5-methoxy-1,6-heptadiene

3-benzyloxy-4-benzyloxymethyl-2-methyl-hept-6-ene-2,5-diol