(2R,3R,5S)-3,5-DiMethyl-1-benzyloxy-2-hydroxy-8-(4-Methoxyphenoxy)-4-octanone

Base Information

• Chemical Name: (2R,3R,5S)-3,5-DiMethyl-1-benzyloxy-2-hydroxy-8-(4-Methoxyphenoxy)-4-octanone
• CAS No.: 276690-15-4
• Molecular Formula: C₂₄H₃₂O₅
• Molecular Weight: 400.515
• Mol file: 276690-15-4.mol

Synonyms:(2R,3R,5S)-(-)-1-Benzyloxyhydroxy-8-(4'-methoxyphenoxy)-3,5-dimethyloctan-4-one

Chemical Property of (2R,3R,5S)-3,5-DiMethyl-1-benzyloxy-2-hydroxy-8-(4-Methoxyphenoxy)-4-octanone

Chemical Property:

• Boiling Point: 562.4±50.0 °C(Predicted)
• PKA: 13.62±0.20(Predicted)
• Density: 1.096±0.06 g/cm3(Predicted)
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

(2R,3R,5S)-3,5-Dimethyl-1-benzyloxy-2-hydroxy-8-(4-methoxyphenoxy)-4-octanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2R,3R,5S)-3,5-Dimethyl-1-benzyloxy-2-hydroxy-8-(4-methoxyphenoxy)-4-octanone is an intermediate in the preparation of Stigmatellin A (S686780).

Technology Process of (2R,3R,5S)-3,5-DiMethyl-1-benzyloxy-2-hydroxy-8-(4-Methoxyphenoxy)-4-octanone

There total 5 articles about (2R,3R,5S)-3,5-DiMethyl-1-benzyloxy-2-hydroxy-8-(4-Methoxyphenoxy)-4-octanone 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: 64.0%

benzyloxyacetoaldehyde (60656-87-3) + (S)-(+)-7-(4'-Methoxyphenoxy)-4-methylheptan-3-one (276690-14-3) → (2R,3R,5S)-(-)-1-Benzyloxyhydroxy-8-(4'-methoxyphenoxy)-3,5-dimethyloctan-4-one (276690-15-4)

Guidance literature:

(S)-(+)-7-(4'-Methoxyphenoxy)-4-methylheptan-3-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1.5h;

benzyloxyacetoaldehyde; In dichloromethane; at -78 ℃; for 2h;

Reference yield:

1-(3-chloropropoxy)-4-methoxybenzene (20744-03-0) → (2R,3R,5S)-(-)-1-Benzyloxyhydroxy-8-(4'-methoxyphenoxy)-3,5-dimethyloctan-4-one (276690-15-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 83 percent / NaI / acetone / 120 h / Heating

2.1: LDA / diethyl ether; hexane / 5 h / 0 °C

2.2: 80 percent / diethyl ether; hexane / -100 - 20 °C

3.1: 87 percent / MMPP / methanol / -15 °C / pH 7

4.1: TiCl₄; DIPEA / CH₂Cl₂ / 1.5 h / -78 °C

4.2: 64 percent / CH₂Cl₂ / 2 h / -78 °C

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium diisopropyl amide; In methanol; diethyl ether; hexane; dichloromethane; acetone; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Oxidation / 4.1: Metallation / 4.2: Aldol reaction;

Reference yield:

4-methoxy-phenol (150-76-5) → (2R,3R,5S)-(-)-1-Benzyloxyhydroxy-8-(4'-methoxyphenoxy)-3,5-dimethyloctan-4-one (276690-15-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / DEAD; PPh₃ / CH₂Cl₂ / 72.5 h / 0 - 20 °C

2.1: 83 percent / NaI / acetone / 120 h / Heating

3.1: LDA / diethyl ether; hexane / 5 h / 0 °C

3.2: 80 percent / diethyl ether; hexane / -100 - 20 °C

4.1: 87 percent / MMPP / methanol / -15 °C / pH 7

5.1: TiCl₄; DIPEA / CH₂Cl₂ / 1.5 h / -78 °C

5.2: 64 percent / CH₂Cl₂ / 2 h / -78 °C

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide; diethylazodicarboxylate; In methanol; diethyl ether; hexane; dichloromethane; acetone; 1.1: Etherification / 2.1: Substitution / 3.1: Metallation / 3.2: Alkylation / 4.1: Oxidation / 5.1: Metallation / 5.2: Aldol reaction;

upstream raw materials:

benzyloxyacetoaldehyde

(S)-(+)-7-(4'-Methoxyphenoxy)-4-methylheptan-3-one

1-(3-chloropropoxy)-4-methoxybenzene

4-methoxy-phenol

Downstream raw materials:

(2R,3S,4S,5S)-(-)-1-Benzyloxy-8-(4'-methoxyphenoxy)-3,5-dimethyloctan-2,4-diol

Refernces