(2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

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Chemical Name:(2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde
CAS No.:248916-36-1
Molecular Formula:C₁₉H₂₆O₂
Molecular Weight:286.414
Hs Code.:

Synonyms:(2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

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Chemical Property of (2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

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Technology Process of (2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

There total 2 articles about (2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde 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: 97.0%

: 248916-35-0
(2R,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butan-1-ol

: 248916-36-1
(2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at -10 - -4 ℃; for 1.5h;
DOI:10.1021/jm980736v

Reference yield:

: (2R/S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

: 248916-36-1
(2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 43 h / Heating

2: 97 percent / SO₃*Py; Et₃N; DMSO / CH₂Cl₂ / 1.5 h / -10 - -4 °C

With lithium aluminium tetrahydride; pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Oxidation;
DOI:10.1021/jm980736v

Reference yield:

: 248916-36-1
(2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

: (3S)-3-((1S,2S)-6-(1-ethoxyethoxy)-1,2,6-trimethylheptyl)-3-methylcyclohexan-1-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: DBU / CH₂Cl₂ / 62 h / 20 °C

2.1: NaBH₄ / methanol / 0.25 h / -10 °C

3.1: 78 percent / pyridine / 24 h / 0 °C

4.1: 80 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

5.1: 9-BBN / tetrahydrofuran / 48 h / Heating

5.2: 95 percent / 30 percent H₂O₂; 6 N aq. NaOH / ethanol / 1.5 h / 55 °C

6.1: 76 percent / imidazole; DMAP / dimethylformamide / 16 h / 20 °C

7.1: 85 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 6 h / Heating

8.1: 93 percent / pyridine / 19 h / 20 °C

9.1: NaH; DMSO / 0.75 h / 20 °C

9.2: 48 percent / dimethylsulfoxide / 0.75 h

10.1: 90 percent / H₂ / 5 percent Rh/Al₂O₃ / ethyl acetate / 4 h / 20 °C / 750.06 Torr

11.1: 50 percent / PDC / CH₂Cl₂ / 24 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexene; palladium dihydroxide; Rh/Al₂O₃; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Isomerization / 2.1: Reduction / 3.1: Tosylation / 4.1: reductive cleavae / 5.1: hydroboration / 5.2: Oxidation / 6.1: silylation / 7.1: debenzylation / 8.1: Tosylation / 9.1: Metallation / 9.2: Substitution / 10.1: Catalytic hydrogenation / 11.1: Oxidation;
DOI:10.1021/jm980736v