methyl (1S^*,2S^*,3S^*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate

Base Information

• Chemical Name: methyl (1S^*,2S^*,3S^*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate
• CAS No.: 80090-55-7
• Molecular Formula: C₁₆H₂₈O₄
• Molecular Weight: 284.396

Synonyms:methyl (1S^*,2S^*,3S^*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate

Chemical Property of methyl (1S^*,2S^*,3S^*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate

Chemical Property:

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Technology Process of methyl (1S^*,2S^*,3S^*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate

There total 13 articles about methyl (1S^*,2S^*,3S^*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate 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: 95.0%

2,3-dihydro-2H-furan (1191-99-7,75454-45-4) + methyl (1R*,2S*,3S*)-2-butyl-3-hydroxy-1-cyclohexanecarboxylate (80090-54-6,84277-34-9,88823-65-8,88823-68-1,90411-07-7) → methyl (1S*,2S*,3S*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate (80090-55-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In chloroform; at 0 ℃; for 2h;

DOI:10.1248/cpb.30.2840

Reference yield: 95.0%

2,3-dihydro-2H-furan (1191-99-7,75454-45-4) + (1R,2S,3S)-2-Butyl-3-hydroxy-cyclohexanecarboxylic acid methyl ester (80090-54-6,84277-34-9,88823-65-8,88823-68-1,90411-07-7) → (1S,2R,3R)-2-Butyl-3-(tetrahydro-furan-2-yloxy)-cyclohexanecarboxylic acid methyl ester (80090-55-7)

Guidance literature:

With pyridinium p-toluenesulfonate;

DOI:10.1246/cl.1981.1409

Reference yield:

1-<3-(tert-butyldimethylsiloxy)cyclohex-1-enyl>ethanone (76711-47-2) → methyl (1S*,2S*,3S*)-2-butyl-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate (80090-55-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / diethyl ether; hexane / -70 - -25 °C

2: 1.) lithium diisopropylamide, 2.) triethylamine / tetrahydrofuran / 1.) -70 deg C, 15 min, -40 deg C, 30 min, 2.) -70 deg C to -10 deg C

3: ozone / hexane / -70 °C

4: diethyl ether

5: 97 percent / 5percent aq. HCl / methanol; tetrahydrofuran / 4 h / Ambient temperature

6: 95 percent / pyridinium p-toluenesulfonate / CHCl₃ / 2 h / 0 °C

With hydrogenchloride; pyridinium p-toluenesulfonate; ozone; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; chloroform;

DOI:10.1248/cpb.30.2840

upstream raw materials:

2,3-dihydro-2H-furan

(1R,2S,3S)-2-Butyl-3-hydroxy-cyclohexanecarboxylic acid methyl ester

1-<3-(tert-butyldimethylsiloxy)cyclohex-1-enyl>ethanone

1-[(1S,2R,3R)-2-Butyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-ethanone

Downstream raw materials:

(1R,2S,3S)-1-Allyl-2-butyl-3-hydroxy-cyclohexanecarboxylic acid methyl ester

(1R,2S,3S)-1-Allyl-2-butyl-3-(tetrahydro-furan-2-yloxy)-cyclohexanecarboxylic acid methyl ester

(1R,2S,3S)-2-Butyl-1-(3-ethoxycarbonyl-propyl)-3-(tetrahydro-furan-2-yloxy)-cyclohexanecarboxylic acid methyl ester

Toluene-4-sulfonic acid (6R,7S,8S)-7-butyl-2-oxo-1-aza-spiro[5.5]undec-8-yl ester

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