5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione

Base Information

• Chemical Name: 5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS No.: 67996-13-8
• Molecular Formula: C₂₃H₂₃NO₆
• Molecular Weight: 409.439
• Mol file: 67996-13-8.mol

Synonyms:5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione

Chemical Property of 5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione

There total 1 articles about 5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione 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: 88.0%

indole (120-72-9) + cycl-isopropylidene malonate (2033-24-1) + 2,5-dimethoxybenzaldehyde (93-02-7) → 5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione (67996-13-8)

Guidance literature:

L-proline; In acetonitrile; at 28 - 30 ℃; for 28h;

Reference yield: 96.0%

5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione (67996-13-8) + tert-butyl alcohol (75-65-0) → 2-tert-butoxycarbonyl-3-(2,5-dimethoxyphenyl)-3-(indol-3-yl)-propionic acid (296235-47-7)

Guidance literature:

In pyridine; for 1.5h; Heating;

DOI:10.1016/S0040-4020(00)00446-4

Reference yield:

5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione (67996-13-8) → (2S*,3S*)-β-(2,5-dimethoxyphenyl)tryptophan tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / pyridine / 1.5 h / Heating

2.1: DPPA; Et₃N / toluene / 2 h / 110 °C

2.2: 90 percent / toluene / 110 °C

3.1: H₂ / 10 percent Pd/C / ethanol; acetic acid

With diphenyl-phosphinic acid; hydrogen; triethylamine; palladium on activated charcoal; In pyridine; ethanol; acetic acid; toluene; 1.1: Ring cleavage / 2.1: Rearrangement / 2.2: Addition / 3.1: Catalytic hydrogenation;

DOI:10.1016/S0040-4020(00)00446-4

upstream raw materials:

indole

cycl-isopropylidene malonate

2,5-dimethoxybenzaldehyde

Downstream raw materials:

2-tert-butoxycarbonyl-3-(2,5-dimethoxyphenyl)-3-(indol-3-yl)-propionic acid

α-N-benzyloxycarbonyl-β-(2,5-dimethoxyphenyl)tryptophan tert-butyl ester