(S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid

Base Information

• Chemical Name: (S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid
• CAS No.: 107514-96-5
• Molecular Formula: C₃₇H₄₆NO₆PSi
• Molecular Weight: 659.835

Synonyms:(S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid

Chemical Property of (S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid

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Technology Process of (S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid

There total 12 articles about (S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 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:

C25H46ClNO6Si2 (107514-95-4) + triphenylphosphine (603-35-0) → (S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid (107514-96-5)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1021/jm00388a022

Reference yield:

diallyl tartarate (57833-54-2,61879-31-0,107596-43-0) → (S)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid (107514-96-5)

Guidance literature:

Multi-step reaction with 4 steps

1: periodic acid / tetrahydrofuran / 1 h

2: 100 percent / toluene / 12 h / Heating

3: thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

4: pyridine / dimethylformamide / 2 h / 80 °C

With pyridine; thionyl chloride; periodic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00388a022

Reference yield:

diallyl tartarate (57833-54-2,61879-31-0,107596-43-0) → (R)-2-{(2S,3S)-1-[Allyloxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid (107514-96-5)

Guidance literature:

Multi-step reaction with 4 steps

1: periodic acid / tetrahydrofuran / 1 h

2: toluene / 12 h / Heating

3: 6.2 g / thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

4: 13.9 g / dimethylformamide / 1.5 h / Ambient temperature

With pyridine; thionyl chloride; periodic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00388a022

upstream raw materials:

C₂₅H₄₆ClNO₆Si₂

triphenylphosphine

diallyl tartarate

(3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one

Downstream raw materials:

(1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

allyl (1R,5R,6S)-2-phenyl-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

allyl (1R,5R,6S)-2-<4'-(hydroxymethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

allyl (1R,5R,6S)-2-phenyl-6-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-methylcarbapen-2-em-3-carboxylate

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