1-Oxa-5-azaspiro[5.5]undec-2-ene-2-carboxylic acid, 5-[(2R)-2-[(2R,3S)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]- 4-oxo-2-azetidinyl]-1-oxopropyl]-4-oxo-3-phenyl-, methyl ester

Base Information

• Chemical Name: 1-Oxa-5-azaspiro[5.5]undec-2-ene-2-carboxylic acid, 5-[(2R)-2-[(2R,3S)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]- 4-oxo-2-azetidinyl]-1-oxopropyl]-4-oxo-3-phenyl-, methyl ester
• CAS No.: 397886-97-4
• Molecular Formula: C31H44N2O7Si
• Molecular Weight: 584.785

Synonyms:

Chemical Property of 1-Oxa-5-azaspiro[5.5]undec-2-ene-2-carboxylic acid, 5-[(2R)-2-[(2R,3S)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]- 4-oxo-2-azetidinyl]-1-oxopropyl]-4-oxo-3-phenyl-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Oxa-5-azaspiro[5.5]undec-2-ene-2-carboxylic acid, 5-[(2R)-2-[(2R,3S)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]- 4-oxo-2-azetidinyl]-1-oxopropyl]-4-oxo-3-phenyl-, methyl ester

There total 5 articles about 1-Oxa-5-azaspiro[5.5]undec-2-ene-2-carboxylic acid, 5-[(2R)-2-[(2R,3S)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]- 4-oxo-2-azetidinyl]-1-oxopropyl]-4-oxo-3-phenyl-, methyl 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: 80.0%

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) + 5-(2-bromo-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester (397886-88-3) → 5-((R)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester (397886-97-4) + 5-((S)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester

Guidance literature:

With zinc; In tetrahydrofuran; Heating;

DOI:10.1055/s-2001-18778

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 5-((R)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester (397886-97-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / Ac₂O; H₂SO₄ / acetic acid

2: 92 percent / pyridine / tetrahydrofuran

3: 80 percent / Zn / tetrahydrofuran / Heating

With pyridine; sulfuric acid; acetic anhydride; zinc; In tetrahydrofuran; acetic acid; 3: Reformatsky-type reaction;

DOI:10.1055/s-2001-18778

Reference yield:

phenylacetonitrile (140-29-4) → 5-((R)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester (397886-97-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / NaOMe / methanol

2: 80 percent / Ac₂O; H₂SO₄ / acetic acid

3: 92 percent / pyridine / tetrahydrofuran

4: 80 percent / Zn / tetrahydrofuran / Heating

With pyridine; sulfuric acid; sodium methylate; acetic anhydride; zinc; In tetrahydrofuran; methanol; acetic acid; 4: Reformatsky-type reaction;

DOI:10.1055/s-2001-18778

upstream raw materials:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

5-(2-bromo-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester

cyclohexanone

phenylacetonitrile

Downstream raw materials:

5-((R)-2-{(2R,3S)-1-Allyloxycarbonylmethyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester

5-{(R)-2-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionyl}-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester

(4R,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

p-nitrobenzyl (4R,5R,6S)-6-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

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