p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide

Base Information

• Chemical Name: p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide
• CAS No.: 158877-16-8
• Molecular Formula: C₂₅H₃₀N₆O₇S₂
• Molecular Weight: 590.681
• Mol file: 158877-16-8.mol

Synonyms:p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide

Chemical Property of p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide

There total 2 articles about p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide 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:

1-(2-hydroxyethyl)-1,2,3-triazole-4-carbaldehyde (158877-12-4) → p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide (158877-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₃N, (CF₃SO₂)2O, 2.) Et₃N / 1.) CH₂Cl₂, -15 deg C - -20 deg C, 3.5 h, 2.) CH₂Cl₂, r.t., overnight

2: 1.) CH₃MgBr / 1.) THF, -78 deg C, 15 min, 2.) THF, CH₂Cl₂, -78 deg C, 10 h

With trifluoromethylsulfonic anhydride; methylmagnesium bromide; triethylamine;

DOI:10.7164/antibiotics.47.1030

Reference yield:

p-methoxybenzyl (3S,5R,6S)-6-bromopenam-3-carboxylate 1,1-dioxide (121370-36-3) + 1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazole-4-carbaldehyde (158877-14-6) → p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide (158877-16-8)

Guidance literature:

With methylmagnesium bromide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 15 min, 2.) THF, CH₂Cl₂, -78 deg C, 10 h;

DOI:10.7164/antibiotics.47.1030

Reference yield: 90.0%

acetic anhydride (108-24-7) + p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-hydroxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide (158877-16-8) → p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-acetoxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide (158877-18-0)

Guidance literature:

With pyridine; In tetrahydrofuran; Ambient temperature;

DOI:10.7164/antibiotics.47.1030

upstream raw materials:

p-methoxybenzyl (3S,5R,6S)-6-bromopenam-3-carboxylate 1,1-dioxide

1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazole-4-carbaldehyde

1-(2-hydroxyethyl)-1,2,3-triazole-4-carbaldehyde

Downstream raw materials:

p-methoxybenzyl (3S,5R,6S)-6-<(1RS)-1-acetoxy-1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methyl>penicillanate 1,1-dioxide

p-methoxybenzyl (3S,5R,6Z)-6-<1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methylene>penicillanate 1,1-dioxide

p-methoxybenzyl (3S,5R,6E)-6-<1-<1-<2-(1-methylimidazol-2-yl)thioethyl>-1,2,3-triazol-4-yl>methylene>penicillanate 1,1-dioxide

p-methoxybenzyl (3S,5R,6Z)-6-<1-<1-<2-(1-methylimidazol-2-yl)sulfonylethyl>-1,2,3-triazol-4-yl>methylene>penicillanate 1,1-dioxide