(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one

Base Information

• Chemical Name: (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one
• CAS No.: 88139-97-3
• Molecular Formula: C₅₃H₅₄N₃O₁₃PSi
• Molecular Weight: 1000.08

Synonyms:

Chemical Property of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one

There total 6 articles about (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-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:

5-bromo-furan-2-carboxylic acid (585-70-6) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one (88139-97-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.5 N NaOH / methanol; H₂O / 5 h / Ambient temperature

2: 67.3 percent / dimethylformamide / 24 h

4: 1) n-BuLi, Mg, 1,2-dibromomethane

With sodium hydroxide; n-butyllithium; 1,2-dibromomethane; magnesium; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

sodium 5-bromo-2-furoate (53708-48-8) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one (88139-97-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 67.3 percent / dimethylformamide / 24 h

3: 1) n-BuLi, Mg, 1,2-dibromomethane

With n-butyllithium; 1,2-dibromomethane; magnesium; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

{(2R,3S)-2-(2-Hydroxy-ethyl)-3-[(R)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-nitro-benzyl ester (88198-12-3) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one (88139-97-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / Jones reagent / acetone

2: 54 percent / Et₃N / 0.67 h / 0 °C

3: 1) n-BuLi, Mg, 1,2-dibromomethane

With n-butyllithium; jones reagent; 1,2-dibromomethane; magnesium; triethylamine; In acetone;

DOI:10.1016/S0040-4020(01)92147-7

upstream raw materials:

((5-bromofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2-pyridylthiocarbonyl)methyl-azetidin-2-one

5-bromo-furan-2-carboxylic acid

methyl 5-bromo-2-furoate

Downstream raw materials:

(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2-hydroxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one

(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-methylsulfonyloxymethyl-5'-furanylcarbonyl)methyl-azetidin-2-one

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