(S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester
• CAS No.: 190007-83-1
• Molecular Formula: C₃₄H₄₂N₂O₆
• Molecular Weight: 574.717
• Mol file: 190007-83-1.mol

Synonyms:(S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester

Chemical Property of (S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester

There total 6 articles about (S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl 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: 90.0%

L-valine benzyl ester (21760-98-5) + (S)-3-Benzyl-4-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxazolidine-2,5-dione (190007-80-8) → (S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester (190007-83-1)

Guidance literature:

In dichloromethane; for 24h; Ambient temperature;

DOI:10.1039/a700815e

Reference yield:

(3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one (190007-78-4) → (S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester (190007-83-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

2: 24 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In phosphate buffer; dichloromethane; 1: Oxidation / 2: Condensation;

DOI:10.1021/jo980354x

Reference yield:

Benzyl-[1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine → (S)-2-[(S)-2-Benzylamino-2-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-3-methyl-butyric acid benzyl ester (190007-83-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 7.91 g / triethylamine / CH₂Cl₂ / 0 - 20 °C

2: 95 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

3: 95 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

4: 24 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; dihydrogen peroxide; triethylamine; potassium bromide; In tetrahydrofuran; phosphate buffer; dichloromethane; water; 1: Cycloaddition / 2: Deacetylation / 3: Oxidation / 4: Condensation;

DOI:10.1021/jo980354x

upstream raw materials:

L-valine benzyl ester

(S)-3-Benzyl-4-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxazolidine-2,5-dione

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

(3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one