(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

Base Information

Chemical Name:(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol
CAS No.:247587-51-5
Molecular Formula:C₂₀H₃₂O₃Si
Molecular Weight:348.558
Hs Code.:

Synonyms:(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

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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 (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

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Technology Process of (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

There total 1 articles about (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol 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: 71.0%

: ((1R,2S,4R,6R)-4-Benzyloxy-1-methyl-7-oxa-bicyclo[4.1.0]hept-2-yloxy)-tert-butyl-dimethyl-silane

: 247587-51-5
(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

Guidance literature:: With 2,2,6,6-tetramethylpiperidinyl-lithium; diethylaluminium chloride; In toluene; benzene; at 0 ℃; for 30h;
DOI:10.1021/jo9908288

Reference yield: 74.0%

: 247587-51-5
(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

: 247587-52-6
(1R,2S,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

: (1R,2R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

Guidance literature:: (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; dihydrogen peroxide; In ethanol; at 20 ℃; for 24h;
DOI:10.1021/jo9908288

Reference yield:

: 247587-51-5
(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

: 247587-60-6
9-[(1S,4R,5S)-5-hydroxy-4-hydroxymethyl-2-cyclohexenyl]adenine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

1.2: 74 percent / 35 percent H₂O₂; 2N NaOH / ethanol / 24 h / 20 °C

2.1: 70 percent / imidazole / dimethylformamide / 20 °C

3.1: 92 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 97 percent / HCOONH₄ / Pd/C / 14 h / Heating

5.1: MnO₂ / CH₂Cl₂ / 21 h / 20 °C

6.1: 91 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h

7.1: 66 percent / PPh₃; DEAD / dioxane / 20 °C

8.1: TFA / H₂O / 20 °C

With 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; ammonium formate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: hydroboration / 1.2: Oxidation / 2.1: Substitution / 3.1: Substitution / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Reduction / 7.1: Substitution / 8.1: Substitution;
DOI:10.1021/jo9908288