{(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester
• CAS No.: 92772-06-0
• Molecular Formula: C₄₃H₄₈N₃O₆PS₃Si
• Molecular Weight: 858.128

Synonyms:

Chemical Property of {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-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 {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

There total 10 articles about {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-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:

p-methoxybenzyl glyoxylate monohydrate (92771-89-6) → {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (92772-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / triethylamine / tetrahydrofuran / Ambient temperature

2: 1.) 2,6-lutidine, thionyl bromide; 2.) 2,6-lutidine / 1.) THF, -35 degC, 30 min; 2.) THF, room temperature

3: 1.) AgNO₃, pyridine; 2.) pyridine / 1.) MeOH/THF, 30 min, room temperature; 2.) CH₂Cl₂, -45 degC to 0 degC, 1 h

4: tert-Bu₄NBr / CH₂Cl₂; H₂O / 2 h / Ambient temperature

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

DOI:10.1248/cpb.33.4382

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (92772-06-0)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazol / dimethylformamide / Ambient temperature

2: acetic acid, tetraethylammonium fluoride dihydrate / tetrahydrofuran / 0.5 h / Ambient temperature

3: 84 percent / triethylamine / tetrahydrofuran / Ambient temperature

4: 1.) 2,6-lutidine, thionyl bromide; 2.) 2,6-lutidine / 1.) THF, -35 degC, 30 min; 2.) THF, room temperature

5: 1.) AgNO₃, pyridine; 2.) pyridine / 1.) MeOH/THF, 30 min, room temperature; 2.) CH₂Cl₂, -45 degC to 0 degC, 1 h

6: tert-Bu₄NBr / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sulfurous dibromide; tetraethylammonium fluoride; silver nitrate; acetic acid; triethylamine; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.33.4382

Reference yield:

(3S,4R)-3-Acetyl-1-(tert-butyl-dimethyl-silanyl)-4-tritylsulfanyl-azetidin-2-one (75939-59-2,102628-05-7) → {(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (92772-06-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 25 percent / NaBH₄ / methanol; tetrahydrofuran / 0.17 h / ice-cooling

2: imidazol / dimethylformamide / Ambient temperature

3: acetic acid, tetraethylammonium fluoride dihydrate / tetrahydrofuran / 0.5 h / Ambient temperature

4: 84 percent / triethylamine / tetrahydrofuran / Ambient temperature

5: 1.) 2,6-lutidine, thionyl bromide; 2.) 2,6-lutidine / 1.) THF, -35 degC, 30 min; 2.) THF, room temperature

6: 1.) AgNO₃, pyridine; 2.) pyridine / 1.) MeOH/THF, 30 min, room temperature; 2.) CH₂Cl₂, -45 degC to 0 degC, 1 h

7: tert-Bu₄NBr / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; dibromo sulfoxide; tetraethylammonium fluoride; silver nitrate; acetic acid; triethylamine; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.33.4382

upstream raw materials:

sodium 1,3,4-thiadiazole-2-thiolate

(3S^*,4R^*)-3-<(R^*)-1-tert-butyldimethylsilyloxyethyl>-4-chloroacetoxythio-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-2-azetidinone

p-methoxybenzyl glyoxylate monohydrate

tert-butyldimethylsilyl chloride

Downstream raw materials:

{(3S,4R)-3-((R)-1-Hydroxy-ethyl)-2-oxo-4-[2-([1,3,4]thiadiazol-2-ylsulfanyl)-acetylsulfanyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

p-methoxybenzyl (5R^*,6S^*)-6-<(R^*)-1-hydroxyethyl>-2-(1,3,4-thiadiazol-2-yl)thiomethylpenem-3-carboxylate

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