allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate

Base Information

• Chemical Name: allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate
• CAS No.: 166187-08-2
• Molecular Formula: C₂₈H₄₁N₃O₅SSi
• Molecular Weight: 559.802

Synonyms:allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate

Chemical Property of allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate

Chemical Property:

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Technology Process of allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate

There total 1 articles about allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate 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: 45.0%

(S)-(+)-α-methylamino-β-phenylpropionamide (17193-30-5) + allyl (5R,6S)-2-<<(methylsulfonyl)oxy>methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate (88585-79-9) → allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate (166187-08-2)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; for 20h; Ambient temperature;

DOI:10.1021/jm00021a013

Reference yield:

allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate (166187-08-2) → (5R,6S)-3-{[((S)-1-Carbamoyl-2-phenyl-ethyl)-methyl-amino]-methyl}-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (1026693-36-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 25 ℃; for 24h;

DOI:10.1021/jm00021a013

Reference yield:

allyl (5R,6S)-2-<methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate (166187-08-2) → (5R,6S)-2-<methyl>-6-((R)-1-hydroxyethyl)penem-3-carboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: CH₃COOH, tetrabutylammonium fluoride / tetrahydrofuran / 24 h / 25 °C

2: 51 percent / triphenylphosphine, tetrakis(triphenylphosphine)palladium, acetic acid / tetrahydrofuran / 0.5 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; In tetrahydrofuran;

DOI:10.1021/jm00021a013

upstream raw materials:

(S)-(+)-α-methylamino-β-phenylpropionamide

allyl (5R,6S)-2-<<(methylsulfonyl)oxy>methyl>-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>penem-3-carboxylate

Downstream raw materials:

(5R,6S)-3-{[((S)-1-Carbamoyl-2-phenyl-ethyl)-methyl-amino]-methyl}-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

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