4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene

Base Information

• Chemical Name: 4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene
• CAS No.: 934279-84-2
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602
• Mol file: 934279-84-2.mol

Synonyms:4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene

Chemical Property of 4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene

There total 5 articles about 4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene 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%

4-methyl-3-hydroxy-2-hydroxymethyl-1-methoxy-4-cyclopentadiene (934279-83-1) + tert-butylchlorodiphenylsilane (58479-61-1) → 4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene (934279-84-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2007.01.037

Reference yield:

2-methyl-3-benzyloxy-4-benzyloxymethyl-5-methoxy-1,6-heptadiene (934279-74-0) → 4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene (934279-84-2)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; ammonia; sodium; 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-2-methyl-hept-6-ene-2,5-diol (934279-80-8) → 4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene (934279-84-2)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; ammonia; sodium; sodium hydride; 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

tert-butylchlorodiphenylsilane

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

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

Downstream raw materials:

(4R,5R)-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-methylcyclopent-2-enone

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