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

Base Information

• Chemical Name: (3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one
• CAS No.: 213480-19-4
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508

Synonyms:(3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one

Chemical Property of (3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one

Chemical Property:

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Technology Process of (3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one

There total 2 articles about (3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one 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:

Benzyl-[1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine + Acetoxyacetyl chloride (13831-31-7) → (3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one (213480-19-4)

Guidance literature:

With triethylamine; In dichloromethane; for 16h;

DOI:10.1039/a700815e

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → (3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one (213480-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 4A MS / CH₂Cl₂ / 1 h / 0 °C

2: 7.91 g / triethylamine / CH₂Cl₂ / 0 - 20 °C

With triethylamine; In dichloromethane; 1: Condensation / 2: Cycloaddition;

DOI:10.1021/jo980354x

Reference yield: 95.0%

(3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one (213480-19-4) → (3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one (190007-78-4)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;

DOI:10.1021/jo980354x

upstream raw materials:

Acetoxyacetyl chloride

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

Downstream raw materials:

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

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

(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

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

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