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

Base Information

• Chemical Name: (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(phenylthiocarbonyl)methyl-azetidin-2-one
• CAS No.: 67520-38-1
• Molecular Formula: C₄₈H₄₀N₃O₁₁PS
• Molecular Weight: 897.899

Synonyms:

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

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

{(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-(phenylthiocarbonyl)methyl-azetidin-2-one (67520-38-1,88198-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Jones reagent / acetone

2: 1.) Et₃N, N-methyl-2-fluoropyridinium iodide, 2.) pyridine / 1.) CH₂Cl₂, 0 deg C, 15 min, R_.T_., 30 min, 2.) 20 min

With pyridine; jones reagent; 2-fluoro-1-methylpyridinium iodide; triethylamine; In acetone;

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

Reference yield:

thiophenol (108-98-5) + {(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-(phenylthiocarbonyl)methyl-azetidin-2-one (67520-38-1,88198-14-5)

Guidance literature:

With pyridine; 2-fluoro-1-methylpyridinium iodide; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 15 min, R_.T_., 30 min, 2.) 20 min;

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

Reference yield:

(3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(phenylthiocarbonyl)methyl-azetidin-2-one (67520-38-1,88198-14-5) → (5R*,6S*)-2-(4'-aminomethylphenyl)-6-<(R*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid (88140-14-1)

Guidance literature:

Multi-step reaction with 6 steps

2: 78 percent / 10percent H₂SO₄ aq. / acetic acid / 0.5 h / Ambient temperature

3: 72.4 percent / Et₃N / CH₂Cl₂ / 0 deg C, 0.5 h, RT, overnight

4: 1) lithium azide, LiBr / 1) DMF, RT, 0.5 h, 2) RT, 2 h

5: 58.4 percent / xylene / 1.5 h / Heating

6: 0.001N HCl / 10percent Pd/C / H₂O; dioxane; ethanol / 0.33 h / 2068.6 Torr

With hydrogenchloride; lithium azide; sulfuric acid; triethylamine; lithium bromide; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; xylene;

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

upstream raw materials:

thiophenol

{(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-pyranyloxymethyl)phenylcarbonyl>methyl-azetidin-2-one

(5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid

sodium (5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylate

o-nitrobenzyl-(5R^*,6S^*)-2-(4'-hydroxymethylphenyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate

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