(4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

Base Information

Chemical Name:(4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one
CAS No.:130595-57-2
Molecular Formula:C₁₄H₂₆O₂Si
Molecular Weight:254.445
Hs Code.:

Synonyms:(4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

Suppliers and Price of (4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

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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 (4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

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Technology Process of (4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

There total 9 articles about (4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one 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: 80.0%

: 130695-77-1
(4S,5R)-5-Hydroxymethyl-4-methyl-2-cyclohexen-1-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 130595-57-2
(4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 10h; Ambient temperature;
DOI:10.1248/cpb.38.1479

Reference yield:

: 88586-06-5
(3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one

: 130595-57-2
(4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1) NaBH₄ / 2) DMF, 140 deg C, 3 h

2: 1.50 g / Raney-Nickel W-1, NaOH / ethanol / 0.17 h / Ambient temperature

3: 82 percent / iodine, KI, NaHCO₃ / CH₂Cl₂; H₂O / 48 h / Ambient temperature

4: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 4 h / Heating

5: 0.787 g / LiAlH₄ / tetrahydrofuran / 1) -78 deg C, 30 min., 2) 0 deg C, 1.5 h

6: 48 percent / 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / dioxane / 48 h / Ambient temperature

7: 80 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; Raney-Nickel W-1; iodine; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.38.1479

Reference yield:

: 102629-35-6
(1R,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid

: 130595-57-2
(4S,5R)-5-<(tert-Butyldimethylsilyloxy)methyl>-4-methyl-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / iodine, KI, NaHCO₃ / CH₂Cl₂; H₂O / 48 h / Ambient temperature

2: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 4 h / Heating

3: 0.787 g / LiAlH₄ / tetrahydrofuran / 1) -78 deg C, 30 min., 2) 0 deg C, 1.5 h

4: 48 percent / 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / dioxane / 48 h / Ambient temperature

5: 80 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; iodine; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.38.1479