(1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde

Base Information

• Chemical Name: (1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde
• CAS No.: 117678-59-8
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.3
• Mol file: 117678-59-8.mol

Synonyms:(1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde

Chemical Property of (1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde

There total 4 articles about (1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde 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:

(1S,2S)-di-(-)-menthyl cyclohex-4-ene-1,2-dicarboxylate (109062-95-5) → (1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde (117678-59-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / LiAlH₄ / diethyl ether / 89 h

2: 32 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 91 h / Ambient temperature

3: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 25 min, 2a) -78 deg C, 5 min, b) to.r.t.

With pyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In diethyl ether;

DOI:10.1021/jm00121a036

Reference yield:

(1S,2S,2'S)-1-(hydroxymethyl)-2-<<(2'-methyl-1-oxobutyl)oxy>methyl>cyclohex-4-ene (117678-57-6) → (1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde (117678-59-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1) CH₂Cl₂, -78 deg C, 25 min, 2a) -78 deg C, 5 min, b) to.r.t.;

DOI:10.1021/jm00121a036

Reference yield:

(4S,5S)-4,5-bis(hydroxymethyl)cyclohexene (15679-27-3) → (1S,2S,2'S)-2-<(2'-methyl-1'-oxobutoxy)methyl>cyclohex-4-enecarboxaldehyde (117678-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 91 h / Ambient temperature

2: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 25 min, 2a) -78 deg C, 5 min, b) to.r.t.

With pyridine; dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine;

DOI:10.1021/jm00121a036

upstream raw materials:

(1S,2S,2'S)-1-(hydroxymethyl)-2-<<(2'-methyl-1-oxobutyl)oxy>methyl>cyclohex-4-ene

(4S,5S)-4,5-bis(hydroxymethyl)cyclohexene

(S)-(+)-2-methylbutyric anhydride

(1S,2S)-di-(-)-menthyl cyclohex-4-ene-1,2-dicarboxylate

Downstream raw materials:

(3R,1'R,2'S,2''S,1'''R)-1'''-(1-naphthyl)ethyl 7-<2'-<(2''-methyl-1''-oxobutoxy)methyl>-1'-cyclohex-4'-enyl>-3-<(tert-butyldimethylsilyl)oxy>-5-oxohept-6-enoate

(3R,1'R,2'S,2''S)-7-<2'-<(2''-methyl-1''-oxobutoxy)methyl>-1'-cyclohexyl>-3-hydroxy-5-oxoheptanoic acid

(3R,1'R,2'S,2''S,1'''R)-1'''-(1-naphthyl)ethyl 7-<2'-<(2''-methyl-1''-oxobutoxy)methyl>-1'-cyclohex-4'-enyl>-3-hydroxy-5-oxohept-6-enoate