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

Base Information

• Chemical Name: (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(2-pyranyloxymethyl)phenylcarbonyl>methyl-azetidin-2-one
• CAS No.: 88139-98-4
• Molecular Formula: C₅₄H₅₀N₃O₁₃P
• Molecular Weight: 979.977

Synonyms:(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(2-pyranyloxymethyl)phenylcarbonyl>methyl-azetidin-2-one

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

Chemical Property:

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

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

4-bromobenzenemethanol (873-75-6) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(2-pyranyloxymethyl)phenylcarbonyl>methyl-azetidin-2-one (88139-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / p-TsOH / CH₂Cl₂ / 2 h / Ambient temperature

With toluene-4-sulfonic acid; In dichloromethane;

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-<4'-(2-pyranyloxymethyl)phenylcarbonyl>methyl-azetidin-2-one (88139-98-4)

Guidance literature:

Multi-step reaction with 3 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:

{(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-<4'-(2-pyranyloxymethyl)phenylcarbonyl>methyl-azetidin-2-one (88139-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 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; 2-fluoro-1-methylpyridinium iodide; triethylamine;

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

upstream raw materials:

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran

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

4-bromobenzenemethanol

{(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'-hydroxymethylphenylcarbonyl)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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