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

Base Information

• Chemical Name: (1S,2S,2'S)-1-(hydroxymethyl)-2-<<(2'-methyl-1-oxobutyl)oxy>methyl>cyclohex-4-ene
• CAS No.: 117678-57-6
• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.316
• Mol file: 117678-57-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (1S,2S,2'S)-1-(hydroxymethyl)-2-<<(2'-methyl-1-oxobutyl)oxy>methyl>cyclohex-4-ene 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: 32.0%

(4S,5S)-4,5-bis(hydroxymethyl)cyclohexene (15679-27-3) + (S)-(+)-2-methylbutyric anhydride (84131-91-9) → (1S,2S,2'S)-1-(hydroxymethyl)-2-<<(2'-methyl-1-oxobutyl)oxy>methyl>cyclohex-4-ene (117678-57-6) + (1S,2S,2'S)-1,2-bis<(2'-methyl-1-oxobutoxy)methyl>cyclohex-4-ene (117678-58-7)

Guidance literature:

With pyridine; dmap; for 91h; Ambient temperature;

DOI:10.1021/jm00121a036

Reference yield:

(1S,2S)-di-(-)-menthyl cyclohex-4-ene-1,2-dicarboxylate (109062-95-5) → (1S,2S,2'S)-1-(hydroxymethyl)-2-<<(2'-methyl-1-oxobutyl)oxy>methyl>cyclohex-4-ene (117678-57-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; dmap; lithium aluminium tetrahydride; 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) → (3R,1'R,2'S,2''S)-7-<2'-<(2''-methyl-1''-oxobutoxy)methyl>-1'-cyclohexyl>-3-hydroxy-5-oxoheptanoic acid (117678-63-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 77 percent / LiBr, NEt₃ / acetonitrile / 16 h / Ambient temperature

3: 80 percent / nBu₄NF*3H₂O, HOAc / tetrahydrofuran / 48 h

4: 89 percent / H₂ / 10percent Pd/C / ethyl acetate / 9 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; acetonitrile;

DOI:10.1021/jm00121a036

upstream raw materials:

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

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

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

Downstream raw materials:

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

(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

(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

Refernces