pivaloyloxymethyl (3S^*,4R^*)-α-<4-(2,3-epoxypropyl)-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone-1-yl>-α-triphenylphosphoranilideneacetate

Base Information

• Chemical Name: pivaloyloxymethyl (3S^*,4R^*)-α-<4-(2,3-epoxypropyl)-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone-1-yl>-α-triphenylphosphoranilideneacetate
• CAS No.: 102990-88-5
• Molecular Formula: C₃₆H₃₈NO₉P
• Molecular Weight: 659.673

Synonyms:

Chemical Property of pivaloyloxymethyl (3S^*,4R^*)-α-<4-(2,3-epoxypropyl)-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone-1-yl>-α-triphenylphosphoranilideneacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pivaloyloxymethyl (3S^*,4R^*)-α-<4-(2,3-epoxypropyl)-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone-1-yl>-α-triphenylphosphoranilideneacetate

There total 8 articles about pivaloyloxymethyl (3S^*,4R^*)-α-<4-(2,3-epoxypropyl)-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone-1-yl>-α-triphenylphosphoranilideneacetate 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:

(3S*,4R*)-4-allyl-1-tert-butyldimethylsilyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone (84829-80-1,84848-59-9,91177-16-1) → 2,2-Dimethyl-propionic acid 2-[(2R,3S)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxiranylmethyl-4-oxo-azetidin-1-yl]-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (102990-88-5,103065-48-1)

Guidance literature:

Multi-step reaction with 4 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

2: acetic acid / BF₃-etherate / CH₂Cl₂ / Ambient temperature

3: 1.) triethylamine, molecular sieves 4A / 1.) THF, room temperature; 2.) DMF, 10 min, ice-cooling, 5 min, room temperature

4: 1.) thionyl chloride, 2,6-lutidine; 2.) 2,6-lutidine / 1.) THF, -20 degC, 30 min; 2.) dioxane, room temperature

With 2,6-dimethylpyridine; thionyl chloride; 4 A molecular sieve; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1248/cpb.33.4361

Reference yield:

(3S*,4R*)-4-allyl-1-tert-butyldimethylsilyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone (84829-80-1,84848-59-9,91177-16-1) → pivaloyloxymethyl (3S*,4R*)-α-<4-(2,3-epoxypropyl)-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone-1-yl>-α-triphenylphosphoranilideneacetate (102990-88-5,103065-48-1)

Guidance literature:

Multi-step reaction with 4 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

2: acetic acid / BF₃-etherate / CH₂Cl₂ / Ambient temperature

3: 1.) triethylamine, molecular sieves 4A / 1.) THF, room temperature; 2.) DMF, 10 min, ice-cooling, 5 min, room temperature

4: 1.) thionyl chloride, 2,6-lutidine; 2.) 2,6-lutidine / 1.) THF, -20 degC, 30 min; 2.) dioxane, room temperature

With 2,6-dimethylpyridine; thionyl chloride; 4 A molecular sieve; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1248/cpb.33.4361

Reference yield:

(3S*,4R*)-1-tert-butyldimethylsilyl-4-(2,3-epoxypropyl)-3-<(4R*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>-2-azetidinone (102990-80-7,103065-36-7,103065-43-6,103065-44-7) → 2,2-Dimethyl-propionic acid 2-[(2R,3S)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxiranylmethyl-4-oxo-azetidin-1-yl]-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (102990-88-5,103065-48-1)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / BF₃-etherate / CH₂Cl₂ / Ambient temperature

2: 1.) triethylamine, molecular sieves 4A / 1.) THF, room temperature; 2.) DMF, 10 min, ice-cooling, 5 min, room temperature

3: 1.) thionyl chloride, 2,6-lutidine; 2.) 2,6-lutidine / 1.) THF, -20 degC, 30 min; 2.) dioxane, room temperature

With 2,6-dimethylpyridine; thionyl chloride; 4 A molecular sieve; acetic acid; triethylamine; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1248/cpb.33.4361

upstream raw materials:

2,2-Dimethyl-propionic acid 2-hydroxy-2-[(2R,3S)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxiranylmethyl-4-oxo-azetidin-1-yl]-acetoxymethyl ester

triphenylphosphine

(3S^*,4R^*)-4-allyl-1-tert-butyldimethylsilyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone

(3S^*,4R^*)-1-tert-butyldimethylsilyl-4-(2,3-epoxypropyl)-3-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>-2-azetidinone

Downstream raw materials:

2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

2,2-Dimethyl-propionic acid 2-[(2R,3S)-2-[2-hydroxy-3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-propyl]-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

2,2-Dimethyl-propionic acid 2-[(2R,3S)-2-[2-hydroxy-3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-propyl]-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

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