(1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol

Base Information

Chemical Name:(1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol
CAS No.:249536-85-4
Molecular Formula:C₂₃H₃₀O₂Si
Molecular Weight:366.576
Hs Code.:

Synonyms:

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Chemical Property of (1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol

Chemical Property:

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Technology Process of (1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol

There total 10 articles about (1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol 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:

: 139616-47-0
methyl (1S)-2-((1R,2R)-2-hydroxycycloheptan-1-yl)oxy-1-methyl-2-cyclopenten-1-carboxylate

: 249536-85-4
(1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 98 percent / I₂; Et₃N / tetrahydrofuran / 24 h / -40 - -20 °C

2.1: 94 percent / DBU / 1 h / 95 - 100 °C

3.1: 85 percent / 10 percent aq. HCl / methanol / 8 h / 20 °C

4.1: 86 percent / NaBH₄; CeCl₃ / methanol / 0.25 h / -40 °C

5.1: 100 percent / 4-DMAP; pyridine / 1 h / 20 °C

6.1: 1,4-benzoquinone; PdCl₂(MeCN)2 / tetrahydrofuran / Heating

6.2: 42 percent / K₂CO₃; MeOH / 1 h / 20 °C

7.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / 20 °C

8.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

9.1: imidazole / dimethylformamide / 2 h / 20 °C

10.1: pyridinium p-toluenesulfonate / methanol / 3 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; iodine; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Iodination / 2.1: Elimination / 3.1: Hydrolysis / 4.1: Luche reduction / 5.1: Acetylation / 6.1: Rearrangement / 6.2: methanolysis / 7.1: Addition / 8.1: Reduction / 9.1: Condensation / 10.1: deprotection;
DOI:10.1248/cpb.47.1256

Reference yield:

: 206755-01-3,249537-15-3
methyl (1S,2S)-2-hydroxy-1-methyl-3-cyclopentenecarboxylate

: 249536-85-4
(1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / 4-DMAP; pyridine / 1 h / 20 °C

2.1: 1,4-benzoquinone; PdCl₂(MeCN)2 / tetrahydrofuran / Heating

2.2: 42 percent / K₂CO₃; MeOH / 1 h / 20 °C

3.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / 20 °C

4.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

5.1: imidazole / dimethylformamide / 2 h / 20 °C

6.1: pyridinium p-toluenesulfonate / methanol / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Acetylation / 2.1: Rearrangement / 2.2: methanolysis / 3.1: Addition / 4.1: Reduction / 5.1: Condensation / 6.1: deprotection;
DOI:10.1248/cpb.47.1256

Reference yield:

: 249536-97-8
methyl (1S,4S)-4-acetoxy-1-methyl-2-cyclopentenecarboxylate

: 249536-85-4
(1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol

Guidance literature:: Multi-step reaction with 5 steps

1: K₂CO₃ / methanol / 1 h / 20 °C

2: pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / 20 °C

3: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

4: imidazole / dimethylformamide / 2 h / 20 °C

5: pyridinium p-toluenesulfonate / methanol / 3 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Addition / 3: Reduction / 4: Condensation / 5: deprotection;
DOI:10.1248/cpb.47.1256