p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate
• CAS No.: 135271-53-3
• Molecular Formula: C₂₅H₃₆ClNO₅Si
• Molecular Weight: 494.103

Synonyms:p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Chemical Property of p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Chemical Property:

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Technology Process of p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

There total 2 articles about p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate 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: 78.0%

p-Methoxybenzyl (1S,5R,6S)-2-Diphenylphosphorylmethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (135237-58-0) → p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (135271-53-3)

Guidance literature:

With lithium chloride; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1248/cpb.39.672

Reference yield:

p-Methoxybenzyl (1S,5R,6S)-2-Hydroxymethyl-1-methyl-6-<(R)-1-trinthylsilyloxyethyl>carbapen-2-em-3-carboxylate (135271-52-2) → p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (135271-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / -50 °C

2: 78 percent / LiCl / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; lithium chloride; In dichloromethane;

DOI:10.1248/cpb.39.672

Reference yield: 89.0%

2-(4-Thioxo-4H-pyridin-1-yl)-ethanesulfonic acid amide (108353-00-0) + p-Methoxybenzyl (1S,5R,6S)-2-Chloromethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate (135271-53-3) → 4-[(4S,5R,6S)-2-(4-Methoxy-benzyloxycarbonyl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-en-3-ylmethylsulfanyl]-1-(2-sulfamoyl-ethyl)-pyridinium; chloride

Guidance literature:

In acetonitrile; for 2h; Ambient temperature;

DOI:10.1248/cpb.39.672

upstream raw materials:

p-Methoxybenzyl (1S,5R,6S)-2-Diphenylphosphorylmethyl-1-methyl-6-<(R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

p-Methoxybenzyl (1S,5R,6S)-2-Hydroxymethyl-1-methyl-6-<(R)-1-trinthylsilyloxyethyl>carbapen-2-em-3-carboxylate

Downstream raw materials:

(1S,5R,6S)-6-<(R)-1-Hydroxyethyl>-1-methyl-2-(1-phenyl-4-pyridinio)thiomethylcarbapen-2-em-3-carboxylate

(1S,5R,6S)-2-<1-(4-Hydroxy)benzoylmethyl-4-pyridinio>thiomethyl-6-<(R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

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