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

Base Information

• Chemical Name: (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2-pyridylthiocarbonyl)methyl-azetidin-2-one
• CAS No.: 88139-89-3
• Molecular Formula: C₄₇H₃₉N₄O₁₁PS
• Molecular Weight: 898.887

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2-pyridylthiocarbonyl)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: 54.0%

2-thiopyridyl chloroformate (73371-99-0) + {(2R,3S)-2-Carboxymethyl-3-[(R)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-nitro-benzyl ester (88198-13-4) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2-pyridylthiocarbonyl)methyl-azetidin-2-one (88139-89-3)

Guidance literature:

With triethylamine; at 0 ℃; for 0.666667h;

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-pyridylthiocarbonyl)methyl-azetidin-2-one (88139-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Jones reagent / acetone

2: 54 percent / Et₃N / 0.67 h / 0 °C

With jones reagent; triethylamine; In acetone;

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

Reference yield:

(3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2-pyridylthiocarbonyl)methyl-azetidin-2-one (88139-89-3) → (5R*,6S*)-2-<4'-(N-methylamidomethyl)phenyl>-6-<(R*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid (88140-25-4)

Guidance literature:

Multi-step reaction with 6 steps

2: 65 percent / conc HCl / dimethylformamide / 0.2 h / Ambient temperature

3: Jones reagent / acetone / 1 h / Ambient temperature

4: 1) carbonyldiimidazole, 2) Et₃N / 1) CH₂Cl₂, 2 h, RT, 2) CH₂Cl₂, 4 h, RT

5: 60 percent / xylene / 4.5 h / 130 °C

6: 10percent Pd/C / tetrahydrofuran; H₂O / 0.17 h / 2068.6 Torr / 0.5 pH 7 "MOPS" buffer

With hydrogenchloride; jones reagent; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; xylene;

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

upstream raw materials:

2-thiopyridyl chloroformate

{(2R,3S)-2-Carboxymethyl-3-[(R)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-nitro-benzyl ester

{(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

Downstream raw materials:

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

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

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

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

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