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

Base Information

• Chemical Name: methyl (1R^*,2S^*,3S^*)-2-butyl-1-(3-ethoxycarbonyl-2-propenyl)-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate
• CAS No.: 80090-58-0
• Molecular Formula: C₂₂H₃₆O₆
• Molecular Weight: 396.524

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about methyl (1R^*,2S^*,3S^*)-2-butyl-1-(3-ethoxycarbonyl-2-propenyl)-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:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (1R,2S,3S)-2-Butyl-1-(2-oxo-ethyl)-3-(tetrahydro-furan-2-yloxy)-cyclohexanecarboxylic acid methyl ester → methyl (1R*,2S*,3S*)-2-butyl-1-(3-ethoxycarbonyl-2-propenyl)-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate (80090-58-0)

Guidance literature:

With sodium hydride; In diethyl ether; at 0 ℃; Yield given; 1.) 0 deg C, 1 h, 2.) 0 deg C, 15 min;

DOI:10.1248/cpb.30.2840

Reference yield:

1-<3-(tert-butyldimethylsiloxy)cyclohex-1-enyl>ethanone (76711-47-2) → methyl (1R*,2S*,3S*)-2-butyl-1-(3-ethoxycarbonyl-2-propenyl)-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate (80090-58-0)

Guidance literature:

Multi-step reaction with 10 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

8: 92 percent / pyridinium p-toluenesulfonate / CHCl₃ / 1 h / 0 °C

9: 1.) N-methylmorpholine N-oxide, osmium tetroxide, 2.) sodium periodate / 1.) THF/water, RT, 15 min, 2.) THF/water, RT, 3.5 h

10: 1.) NaH / diethyl ether / 0 °C / 1.) 0 deg C, 1 h, 2.) 0 deg C, 15 min

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; pyridinium p-toluenesulfonate; sodium hydride; ozone; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; chloroform;

DOI:10.1248/cpb.30.2840

Reference yield:

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 (1R*,2S*,3S*)-2-butyl-1-(3-ethoxycarbonyl-2-propenyl)-3-(2-tetrahydrofuranyloxy)-1-cyclohexanecarboxylate (80090-58-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / pyridinium p-toluenesulfonate / CHCl₃ / 2 h / 0 °C

3: 92 percent / pyridinium p-toluenesulfonate / CHCl₃ / 1 h / 0 °C

4: 1.) N-methylmorpholine N-oxide, osmium tetroxide, 2.) sodium periodate / 1.) THF/water, RT, 15 min, 2.) THF/water, RT, 3.5 h

5: 1.) NaH / diethyl ether / 0 °C / 1.) 0 deg C, 1 h, 2.) 0 deg C, 15 min

With sodium periodate; osmium(VIII) oxide; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; In diethyl ether; chloroform;

DOI:10.1248/cpb.30.2840

upstream raw materials:

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

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

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

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

Downstream raw materials:

(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

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

(6R^*,7S^*,8S^*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one

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