allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Base Information

Chemical Name:allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
CAS No.:304655-63-8
Molecular Formula:C₃₂H₃₉N₃O₈S
Molecular Weight:625.743
Hs Code.:

allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Synonyms:allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

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Chemical Property of allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

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Technology Process of allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

There total 33 articles about allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-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:

: 133808-94-3
allyl (1R,5R,6S)-2-(diphenoxyphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate

: 262845-95-4
(2R,4S)-2-[4-(Allyloxycarbonylamino-methyl)-phenyl]-4-mercapto-pyrrolidine-1-carboxylic acid allyl ester

: 304655-63-8
allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃;
DOI:10.1016/S0960-894X(99)00657-5

Reference yield:

: 170719-60-5
(2R,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

: 304655-63-8
allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: aq. NaOH / methanol / 0.33 h / 0 °C

2: 222 mg / iPr₂NEt / acetonitrile / 4 °C

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; In methanol; acetonitrile;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: 87736-74-1
4-(tert-butyldimethylsiloxymethyl)bromobenzene

: 304655-63-8
allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 18 steps

1: 88 percent / n-BuLi / tetrahydrofuran / -70 °C

2: 88 percent / tetrapropylammonium perruthenate; 4-methylmorpholine / CH₂Cl₂

3: NaBH₄ / methanol / 0 °C

4: TEA / CH₂Cl₂ / 0 °C

5: NaN₃ / dimethylformamide / 50 °C

6: PPh₃; water / tetrahydrofuran / 20 °C

7: TEA / tetrahydrofuran / 0 °C

8: n-Bu₄NF / tetrahydrofuran / 0 °C

9: TEA / CH₂Cl₂ / 0 °C

10: NaN₃ / dimethylformamide / 20 °C

11: PPh₃; H₂₀ / tetrahydrofuran / 20 °C

12: TEA / tetrahydrofuran / 0 °C

13: p-TsOH / methanol / 20 °C

14: TEA / CH₂Cl₂ / 0 °C

15: 97 percent / t-BuOK / tetrahydrofuran / -20 °C

16: 87 percent / dimethylformamide / 65 - 70 °C

17: NaOH / methanol / 0 °C

18: i-Pr₂EtN / acetonitrile / 0 °C

With 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; sodium azide; tetrapropylammonium perruthennate; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1248/cpb.48.310