(1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde

Base Information

• Chemical Name: (1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde
• CAS No.: 517867-54-8
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• Mol file: 517867-54-8.mol

Synonyms:(1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde

Chemical Property of (1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde

There total 3 articles about (1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde 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:

cyclohex-1-enylmethyltrimethylsilane (58541-14-3) + (1S,2S,3S)-(-)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester (343984-02-1) → (1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde (517867-54-8) + (1'S,2R,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde

Guidance literature:

cyclohex-1-enylmethyltrimethylsilane; (1S,2S,3S)-(-)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 12h;

With barium dihydroxide; In methanol; at 0 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1021/ol034141s

Reference yield:

2-furoic acid methyl ester (611-13-2) → (1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde (517867-54-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 53 percent / Cu(OTf)2; (S,S)-2,2-bis(4,4-di-t-Bu-2-1,3-oxazolin-2-yl)propane; PhNHNH₂ / CH₂Cl₂ / 12 h / 0 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 94 percent / Me₂S / CH₂Cl₂ / 24 h / -78 - 20 °C

3.1: BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

3.2: Ba(OH)2*8 H₂O / methanol / 2 h / 0 °C

With (S,S)-2,2-bis(4,4-di-t-Bu-2-1,3-oxazolin-2-yl)propane; boron trifluoride diethyl etherate; copper(II) bis(trifluoromethanesulfonate); ozone; phenylhydrazine; In dichloromethane;

DOI:10.1021/ol034141s

Reference yield:

(1S,5S,6S)-(-)-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylic acid 6-ethyl ester 3-methyl ester (302349-65-1) → (1'R,2S,3R)-2-(2'-methylenecyclohexyl)-5-oxotetrahydrofuran-3-carbaldehyde (517867-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 94 percent / Me₂S / CH₂Cl₂ / 24 h / -78 - 20 °C

2.1: BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

2.2: Ba(OH)2*8 H₂O / methanol / 2 h / 0 °C

With boron trifluoride diethyl etherate; ozone; In dichloromethane;

DOI:10.1021/ol034141s

upstream raw materials:

cyclohex-1-enylmethyltrimethylsilane

(1S,2S,3S)-(-)-oxalic acid 2-ethoxycarbonyl-3-formylcyclopropyl ester methyl ester

2-furoic acid methyl ester

(1S,5S,6S)-(-)-2-oxabicyclo[3.1.0]hex-3-ene-3,6-dicarboxylic acid 6-ethyl ester 3-methyl ester