p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate
CAS No.:1026234-25-2
Molecular Formula:C₁₈H₁₆N₂O₆
Molecular Weight:356.335
Hs Code.:

Synonyms:p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

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Chemical Property of p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

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Technology Process of p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

There total 2 articles about p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]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: 85.0%

: (5R,6S)-3-Ethynyl-7-oxo-6-((R)-1-trimethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

: 1026234-25-2
p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 1.75h;
DOI:10.7164/antibiotics.51.210

Reference yield:

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 1026234-25-2
p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C

1.2: Et₃N / tetrahydrofuran / 0.33 h / -78 °C

1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl₂ / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C

2.1: 85 percent / AcOH; aq. Bu₄NF / tetrahydrofuran / 1.75 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; acetic acid; diisopropylamine; In tetrahydrofuran; 1.1: Addition / 1.2: Etherification / 1.3: Addition / 2.1: Hydrolysis;
DOI:10.7164/antibiotics.51.210