allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]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-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
CAS No.:312297-55-5
Molecular Formula:C₃₄H₄₂N₄O₉S
Molecular Weight:682.795
Hs Code.:

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

There total 8 articles about allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]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

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

: 312297-55-5
allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]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 - 4 ℃;
DOI:10.1016/S0040-4020(00)00685-2

Reference yield:

: Thioacetic acid S-{(3S,5R)-5-[4-((S)-1-amino-2-carbamoyl-ethyl)-phenyl]-pyrrolidin-3-yl} ester

: 312297-55-5
allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 863 mg / Et₃N / CH₂Cl₂ / -10 °C

2: aq. NaOH / methanol / 0.5 h / 0 °C

3: 4.23 g / DIPEA / acetonitrile / 0 - 4 °C

With sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile; 1: Condensation / 2: Hydrolysis / 3: Substitution;
DOI:10.1016/S0040-4020(00)00685-2

Reference yield:

: 312297-72-6
(2R,4R)-1-tert-butoxycarbonyl-2-[4-[(S)-1-tert-butoxycarbonylamino-2-carbonylethyl]phenyl]-4-hydroxypyrrolidine

: 312297-55-5
allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N / tetrahydrofuran / 0.33 h / -20 °C

2: aq. NH₃ / tetrahydrofuran

3: 82.6 percent / dimethylformamide / 10 h / 55 °C

4: HCl / ethyl acetate / 6 h / 20 °C

5: 863 mg / Et₃N / CH₂Cl₂ / -10 °C

6: aq. NaOH / methanol / 0.5 h / 0 °C

7: 4.23 g / DIPEA / acetonitrile / 0 - 4 °C

With hydrogenchloride; ammonium hydroxide; sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Substitution / 3: Substitution / 4: amide cleavage / 5: Condensation / 6: Hydrolysis / 7: Substitution;
DOI:10.1016/S0040-4020(00)00685-2