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

Base Information

• Chemical Name: 7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-6-methyl-9a-carbobenzoxy-1,8-dioxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine
• CAS No.: 139976-61-7
• Molecular Formula: C₂₆H₃₈N₂O₅Si
• Molecular Weight: 486.684
• Mol file: 139976-61-7.mol

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

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

There total 2 articles about 7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-6-methyl-9a-carbobenzoxy-1,8-dioxoazetidino<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:

(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-<(tert-butyldimethylsilyl)oxy>ethyl>>-6-methyl-9a-carbobenzoxy-1,8-dioxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine (139976-61-7)

Guidance literature:

Multi-step reaction with 3 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

With lithium borohydride; di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; pyridinium p-toluenesulfonate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1021/jo00035a019

Reference yield:

2,2-Dihydroxy-3-oxo-pent-4-enoic acid benzyl ester + 3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-azido-2-methylethyl)>azetidin-2-one (139976-60-6) → 7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-6-methyl-9a-carbobenzoxy-1,8-dioxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine (139976-61-7)

Guidance literature:

With pyridinium p-toluenesulfonate; Yield given. Multistep reaction; 1) CH₂Cl₂, a) 15 min, 0 deg C, b) -25 deg C, overnight, 2) CH₂Cl₂, 15 min, reflux;

DOI:10.1021/jo00035a019

Reference yield: 93.0%

7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-6-methyl-9a-carbobenzoxy-1,8-dioxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine (139976-61-7) → 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)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1021/jo00035a019

upstream raw materials:

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

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

Downstream 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

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