{(2R,3S)-3-((S)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: {(2R,3S)-3-((S)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester
• CAS No.: 97129-45-8
• Molecular Formula: C₃₉H₃₆N₅O₈PS₂
• Molecular Weight: 797.849

Synonyms:

Chemical Property of {(2R,3S)-3-((S)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,3S)-3-((S)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

There total 14 articles about {(2R,3S)-3-((S)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester 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: 95.0%

sodium 1-methyl-1H-tetrazole-5-thiolate (51138-06-8) + p-methoxybenzyl α-<(3S*,4R*)-4-chloroacetylthio-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinon-1-yl>-α-triphenylphosphoranylideneacetate (97129-43-6,97169-66-9,103065-71-0,103067-70-5) → {(2R,3S)-3-((S)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (97129-45-8,97169-67-0,103065-77-6)

Guidance literature:

tetrabutylammomium bromide; In dichloromethane; water; for 2h; Ambient temperature;

DOI:10.1248/cpb.33.4371

Reference yield:

Hydroxy-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester (102991-09-3,103065-69-6) → {(2R,3S)-3-((R)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (97129-45-8,97169-67-0,103065-77-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine, thionyl bromide / tetrahydrofuran / 0.5 h / -30 °C

2: 2,6-lutidine / dioxane / 10 h / Ambient temperature

3: 1.) AgNO₃; 2.) pyridine / 1.) THF/water, ice-cooling, 3 h; 2.) CH₂Cl₂, -40 degC, 1 h

4: tetra-n-butylammonium bromide / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; dibromo sulfoxide; silver nitrate; tetrabutylammomium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1248/cpb.33.4371

Reference yield:

Hydroxy-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester (102991-09-3,103065-69-6) → {(2R,3S)-3-((S)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (97129-45-8,97169-67-0,103065-77-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine, thionyl bromide / tetrahydrofuran / 0.5 h / -30 °C

2: 2,6-lutidine / dioxane / 10 h / Ambient temperature

3: 1.) AgNO₃; 2.) pyridine / 1.) THF/water, ice-cooling, 3 h; 2.) CH₂Cl₂, -40 degC, 1 h

4: 95 percent / tetra-n-butylammonium bromide / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; dibromo sulfoxide; silver nitrate; tetrabutylammomium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1248/cpb.33.4371

upstream raw materials:

sodium 1-methyl-1H-tetrazole-5-thiolate

p-methoxybenzyl α-<(3S^*,4R^*)-4-chloroacetylthio-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinon-1-yl>-α-triphenylphosphoranylideneacetate

Hydroxy-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester

Bromo-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester

Downstream raw materials:

p-methoxybenzyl (5R^*,6S^*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-(1-methyl-1H-tetrazol-5-yl)-thiomethylpenem-3-carboxylate

p-methoxybenzyl 6-<(E)-1-(hydroxymethyl)ethylidene>-2-(1-methyl-1H-tetrazol-5-yl)thiomethylpenem-3-carboxylate

(5S,6R)-6-((R)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

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