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

Base Information

• Chemical Name: (3S^*,4R^*)-3-<(R^*)-1-tert-butyldimethylsilyloxyethyl>-4-chloroacetoxythio-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-2-azetidinone
• CAS No.: 92771-92-1
• Molecular Formula: C₄₁H₄₇ClNO₆PSSi
• Molecular Weight: 776.406

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3S^*,4R^*)-3-<(R^*)-1-tert-butyldimethylsilyloxyethyl>-4-chloroacetoxythio-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-2-azetidinone 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-butyldimethylsilyloxyethyl>-4-chloroacetoxythio-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-2-azetidinone (92771-92-1,102680-82-0)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; 2,6-dimethylpyridine; dibromo sulfoxide; silver nitrate; triethylamine; In tetrahydrofuran;

DOI:10.1248/cpb.33.4382

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3S*,4R*)-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-chloroacetoxythio-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-2-azetidinone (92771-92-1,102680-82-0)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1248/cpb.33.4382

Reference yield:

(3S*,4R*)-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-triphenylmethylthio-2-azetidinone (87996-93-8,88035-31-8,93603-69-1) → (3S*,4R*)-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-chloroacetoxythio-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-2-azetidinone (92771-92-1,102680-82-0)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; 2,6-dimethylpyridine; dibromo sulfoxide; silver nitrate; triethylamine; In tetrahydrofuran;

DOI:10.1248/cpb.33.4382

upstream raw materials:

(3S^*,4R^*)-3-<(R^*)-1-hydroxyethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-triphenylmethylthio-2-azetidinone

chloroacetyl chloride

p-methoxybenzyl glyoxylate monohydrate

tert-butyldimethylsilyl chloride

Downstream raw materials:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetylsulfanyl]-4-oxo-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

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

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

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