allyl (1R,5S,6S)-2-[(3S,5R)-5-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidin-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)-5-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
CAS No.:442887-37-8
Molecular Formula:C₃₂H₄₅N₃O₈S
Molecular Weight:631.791
Hs Code.:

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

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

There total 17 articles about allyl (1R,5S,6S)-2-[(3S,5R)-5-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidin-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:

: 442681-67-6
(2R,4R)-1-tert-butoxycarbonyl-2-[(E)-2-(ethoxycarbonyl)vinyl]-4-hydroxypyrrolidine

: 442887-37-8
allyl (1R,5S,6S)-2-[(3S,5R)-5-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 15 steps

1.1: PPh₃; diisopropyl azodicarboxylate; AcOH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 82.2 percent / aq. NaOH / ethanol / 0.17 h / 20 °C

2.1: 78.9 percent / imidazole / dimethylformamide / 3 h / 20 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: TBAB / tetrahydrofuran / 24 h / 50 °C

4.1: 27.94 percent / NaCl / dimethylsulfoxide; H₂O / 3 h / 160 °C

5.1: 9.09 g / LiAlH₄ / pyridine / 0.5 h / -20 °C

6.1: 74.9 percent / Me₃P / tetrahydrofuran / 13 h / 50 °C

7.1: 97.5 percent / HgCl₂; Mg / tetrahydrofuran; methanol / 1 h / 18 °C

8.1: H₂ / Raney Ni / methanol / 22 h / 20 °C / 2660 Torr

9.1: 5.74 g / iPr₂NEt / tetrahydrofuran; H₂O / 0 °C

10.1: 10 percent HCl / methanol / 20 h / 20 °C

10.2: 80.7 percent / aq. NaOH / dioxane; H₂O / 20 °C / pH 8.5

11.1: 93.7 percent / PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

12.1: 100 percent / aq. NaOH / methanol / 0.5 h / 20 °C

13.1: PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

14.1: aq. NaOH / tetrahydrofuran / 0.33 h / 0 °C

15.1: 2.37 g / iPr₂NEt / acetonitrile / 4 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen; sodium hydride; magnesium; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium chloride; mercury dichloride; trimethylphosphane; nickel; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 3.2: Michael addition / 11.1: Mitsunobu reaction / 13.1: Mitsunobu reaction;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: 442681-68-7
(2R,4S)-1-tert-butoxycarbonyl-2-[(E)-2-(ethoxycarbonyl)vinyl]-4-hydroxypyrrolidine

: 442887-37-8
allyl (1R,5S,6S)-2-[(3S,5R)-5-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1.1: 78.9 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: TBAB / tetrahydrofuran / 24 h / 50 °C

3.1: 27.94 percent / NaCl / dimethylsulfoxide; H₂O / 3 h / 160 °C

4.1: 9.09 g / LiAlH₄ / pyridine / 0.5 h / -20 °C

5.1: 74.9 percent / Me₃P / tetrahydrofuran / 13 h / 50 °C

6.1: 97.5 percent / HgCl₂; Mg / tetrahydrofuran; methanol / 1 h / 18 °C

7.1: H₂ / Raney Ni / methanol / 22 h / 20 °C / 2660 Torr

8.1: 5.74 g / iPr₂NEt / tetrahydrofuran; H₂O / 0 °C

9.1: 10 percent HCl / methanol / 20 h / 20 °C

9.2: 80.7 percent / aq. NaOH / dioxane; H₂O / 20 °C / pH 8.5

10.1: 93.7 percent / PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

11.1: 100 percent / aq. NaOH / methanol / 0.5 h / 20 °C

12.1: PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

13.1: aq. NaOH / tetrahydrofuran / 0.33 h / 0 °C

14.1: 2.37 g / iPr₂NEt / acetonitrile / 4 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen; sodium hydride; magnesium; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium chloride; mercury dichloride; trimethylphosphane; nickel; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 2.2: Michael addition / 10.1: Mitsunobu reaction / 12.1: Mitsunobu reaction;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: (2R,4R)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-formyl-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester

: 442887-37-8
allyl (1R,5S,6S)-2-[(3S,5R)-5-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 17 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 94.8 percent / tetrahydrofuran / 0.17 h / 0 - 5 °C

2.1: 98.1 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

3.1: PPh₃; diisopropyl azodicarboxylate; AcOH / tetrahydrofuran / 0.5 h / 0 °C

3.2: 82.2 percent / aq. NaOH / ethanol / 0.17 h / 20 °C

4.1: 78.9 percent / imidazole / dimethylformamide / 3 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

5.2: TBAB / tetrahydrofuran / 24 h / 50 °C

6.1: 27.94 percent / NaCl / dimethylsulfoxide; H₂O / 3 h / 160 °C

7.1: 9.09 g / LiAlH₄ / pyridine / 0.5 h / -20 °C

8.1: 74.9 percent / Me₃P / tetrahydrofuran / 13 h / 50 °C

9.1: 97.5 percent / HgCl₂; Mg / tetrahydrofuran; methanol / 1 h / 18 °C

10.1: H₂ / Raney Ni / methanol / 22 h / 20 °C / 2660 Torr

11.1: 5.74 g / iPr₂NEt / tetrahydrofuran; H₂O / 0 °C

12.1: 10 percent HCl / methanol / 20 h / 20 °C

12.2: 80.7 percent / aq. NaOH / dioxane; H₂O / 20 °C / pH 8.5

13.1: 93.7 percent / PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

14.1: 100 percent / aq. NaOH / methanol / 0.5 h / 20 °C

15.1: PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

16.1: aq. NaOH / tetrahydrofuran / 0.33 h / 0 °C

17.1: 2.37 g / iPr₂NEt / acetonitrile / 4 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; magnesium; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium chloride; mercury dichloride; trimethylphosphane; nickel; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 1.2: Horner-Emmons reaction / 5.2: Michael addition / 13.1: Mitsunobu reaction / 15.1: Mitsunobu reaction;
DOI:10.1016/S0968-0896(01)00430-8