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

Base Information

Chemical Name:(4R,5R)-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-methylcyclopent-2-enone
CAS No.:934279-85-3
Molecular Formula:C₂₄H₃₀O₃Si
Molecular Weight:394.586
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 6 articles about (4R,5R)-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-methylcyclopent-2-enone 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: 88.0%

: 934279-84-2
4-methyl-3-hydroxy-2-tert-butyldiphenylsilyloxymethyl-1-methoxy-4-cyclopentadiene

: 934279-85-3
(4R,5R)-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-methylcyclopent-2-enone

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2007.01.037

Reference yield:

: 934279-80-8
3-benzyloxy-4-benzyloxymethyl-2-methyl-hept-6-ene-2,5-diol

: 934279-85-3
(4R,5R)-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-methylcyclopent-2-enone

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; ammonia; sodium; sodium hydride; Dess-Martin periodane; 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

Reference yield:

: 934279-81-9
3-benzyloxy-4-benzyloxymethyl-5-methoxy-2-methyl-hept-6-ene-2-ol

: 934279-85-3
(4R,5R)-5-O-tert-butyldiphenylsilyloxymethyl-4-methoxy-2-methylcyclopent-2-enone

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; ammonia; sodium; Dess-Martin periodane; 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