N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester

Base Information

• Chemical Name: N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester
• CAS No.: 108149-66-2
• Molecular Formula: C₂₁H₂₈F₃NO₆
• Molecular Weight: 447.452
• Mol file: 108149-66-2.mol

Synonyms:N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester

Chemical Property of N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester

There total 6 articles about N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher 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:

(S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6) + 4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (108149-63-9) → N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester (108149-66-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 4.5h; Ambient temperature;

DOI:10.1021/jo00388a004

Reference yield:

(S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester (95715-86-9,108149-60-6) → N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester (108149-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether

2: DMAP; DCC / CH₂Cl₂ / 20 °C

With dmap; lithium aluminium tetrahydride; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane;

DOI:10.1021/jo026653a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-<(1,1-Dimethylethoxy)carbonyl>-L-serinol (S)-Mosher ester (108149-66-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1 N NaOH / dioxane / 1.) 5 deg C, 30 min, 2.) RT, 3.5 h

2: diethyl ether / 0.5 h / 0 °C

3: TsOH*H₂O / benzene / 0.5 h

4: 76 percent / diisobutylaluminum hydride (DIBAL) / toluene / 2 h / -78 °C

5: 71 percent / NaBH₄ / propan-2-ol; tetrahydrofuran / 0.5 h

6: 104 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 4.5 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; isopropyl alcohol; toluene; benzene;

DOI:10.1021/jo00388a004

upstream raw materials:

(S)-Mosher acid

4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester

di-tert-butyl dicarbonate