7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine

Base Information

• Chemical Name: 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine
• CAS No.: 139976-63-9
• Molecular Formula: C₂₀H₂₆N₂O₅
• Molecular Weight: 374.437
• Mol file: 139976-63-9.mol

Synonyms:7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine

Chemical Property of 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine

There total 4 articles about 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine 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: 84.0%

7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine (139976-62-8) → 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine (139976-63-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jo00035a019

Reference yield:

(3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone (109715-77-7) → 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine (139976-63-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / LiBH₄ / tetrahydrofuran / 5 h / a) -10 deg C - 0 deg C, b) -25 deg C, overnight

2: 95 percent / triphenylphosphine, diisopropylazodicarboxylate (DIAD), diphenylphosphoryl azide / tetrahydrofuran / 0.17 h / 0 deg C to room temperature

3: 2) pyridinium p-toluene sulfonate (PPTS) / 1) CH₂Cl₂, a) 15 min, 0 deg C, b) -25 deg C, overnight, 2) CH₂Cl₂, 15 min, reflux

4: 93 percent / L-selectride / tetrahydrofuran / 0.17 h / -78 °C

5: 84 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 4 h / Ambient temperature

With lithium borohydride; di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; L-Selectride; triphenylphosphine; In tetrahydrofuran;

DOI:10.1021/jo00035a019

Reference yield:

3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-azido-2-methylethyl)>azetidin-2-one (139976-60-6) → 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine (139976-63-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2) pyridinium p-toluene sulfonate (PPTS) / 1) CH₂Cl₂, a) 15 min, 0 deg C, b) -25 deg C, overnight, 2) CH₂Cl₂, 15 min, reflux

2: 93 percent / L-selectride / tetrahydrofuran / 0.17 h / -78 °C

3: 84 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 4 h / Ambient temperature

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; L-Selectride; In tetrahydrofuran;

DOI:10.1021/jo00035a019

upstream raw materials:

7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine

(3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone

3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-azido-2-methylethyl)>azetidin-2-one

7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-6-methyl-9a-carbobenzoxy-1,8-dioxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine