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

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Chemical Name:(2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid
CAS No.:248916-54-3
Molecular Formula:C₁₉H₂₆O₃
Molecular Weight:302.414
Hs Code.:

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

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Chemical Property of (2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

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Technology Process of (2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

There total 9 articles about (2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid 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: 60.0%

: 248916-55-4
(2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butan-1-ol

: 248916-54-3
(2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone;
DOI:10.1021/jm980736v

Reference yield:

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

: 248916-54-3
(2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: LiAlH₄ / tetrahydrofuran / 43 h / Heating

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

3: DBU / CH₂Cl₂ / 62 h / 20 °C

4: NaBH₄ / methanol / 0.25 h / -10 °C

5: 60 percent / aq. CrO₃; H₂SO₄ / acetone

With chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; pyridine-SO₃ complex; sulfuric acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; 1: Reduction / 2: Oxidation / 3: Isomerization / 4: Reduction / 5: Oxidation;
DOI:10.1021/jm980736v

Reference yield:

: 128693-47-0
(R)-4-(Benzyloxy)-3-methylbutanoic acid

: 248916-54-3
(2S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

2.1: i-Pr₂NH; n-BuLi; HMPA / hexane; tetrahydrofuran / 0.5 h / -78 - -50 °C

2.2: hexane; tetrahydrofuran / 0.33 h

3.1: hexane; tetrahydrofuran / 16 h / Heating

4.1: 5 percent aq. HCl / 1 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; 1.1: Esterification / 2.1: Metallation / 2.2: silylation / 3.1: Rearrangement / 4.1: Hydrolysis;
DOI:10.1021/jm980736v