(1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester

Base Information

• Chemical Name: (1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester
• CAS No.: 135504-89-1
• Molecular Formula: C₃₇H₃₆O₈
• Molecular Weight: 608.688
• Mol file: 135504-89-1.mol

Synonyms:

Chemical Property of (1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester

There total 1 articles about (1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester 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:

(R)-2-acetoxy-1,1,2-triphenylethanol (95061-47-5) + 1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde (88818-28-4) → (1'R,3S)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester (135504-89-1) + (1'R,3R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester (135504-88-0)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, 0 deg C, 30 min., 2) THF, -78 deg C, 24 h;

Reference yield:

(1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester (135504-88-0,135504-89-1) → shikonin (517-89-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / KOH / methanol; H₂O / 2.5 h / Heating

2: p-toluenesulfonic acid / 48 h / Ambient temperature

3: 4-(dimethylamino)pyridine, imdazole / dimethylformamide / 72 h / Ambient temperature

4: diisobutylaluminum hydride / CH₂Cl₂ / 29 h / -78 °C

5: 1) 1.6M n-BuLi / 1) Et₂O, 0 deg C, 1.5 h, 2) Et₂O, r.t., 24 h

6: 54 percent / 4)2(NO₃)6> / acetonitrile; CHCl₃; H₂O / 1 h / 0 °C

7: 29 percent / AgO, 6 N HNO₃ / dioxane / 0.75 h / Ambient temperature

8: 51 percent / (n-C₄H₉)4NF*3H₂O / tetrahydrofuran / 40 h / Ambient temperature

With 1H-imidazole; dmap; silver(II) oxide; potassium hydroxide; n-butyllithium; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; nitric acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

(R)-2-acetoxy-1,1,2-triphenylethanol

1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde

Downstream raw materials:

shikonin

Refernces