4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate
• CAS No.: 258840-07-2
• Molecular Formula: C₂₃H₂₂N₄O₆S₂
• Molecular Weight: 514.583

Synonyms:4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

Chemical Property of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

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Technology Process of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

There total 2 articles about 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-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:

7-Methylthio-2-(tri-n-butyl-stannyl)imidazo[5,1-b]thiazole (258838-84-5) + (4R,5R,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (154428-43-0) → 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (258840-07-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; zinc(II) chloride; In 1-methyl-pyrrolidin-2-one; at 50 ℃;

DOI:10.1016/j.bmcl.2008.11.039

Reference yield:

7-Methylthio-2-(tri-n-butyl-stannyl)imidazo[5,1-b]thiazole (258838-84-5) + p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate (90822-25-6) → 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (258840-07-2)

Guidance literature:

Reference yield: 61.0%

4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (258840-07-2) + 1,3-bis-(bromomethyl)benzene (626-15-3) → 4-Nitrobenzyl (1S,5R,6S)-2-[6-(3-bromomethyl-benzyl)-7-methylthioimidazo[5,1-b]thiazolium-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate bromide + 2Br(1-)*C54H52N8O12S4(2+)

Guidance literature:

In chloroform; acetonitrile; at 20 ℃;

DOI:10.1016/j.bmcl.2008.11.039

upstream raw materials:

7-Methylthio-2-(tri-n-butyl-stannyl)imidazo[5,1-b]thiazole

p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate

(4R,5R,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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