[(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester
• CAS No.: 99440-90-1
• Molecular Formula: C₂₁H₂₆N₂O₈
• Molecular Weight: 434.446

Synonyms:[(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Chemical Property of [(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

There total 20 articles about [(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester 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:

Oxo-acetic acid cyclohex-3-enyl ester (99440-80-9) → [(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (99440-90-1)

Guidance literature:

Multi-step reaction with 18 steps

1: 60 percent / SnCl₄ / nitromethane / Ambient temperature

2: 86 percent / CrO₃, pyridine / CH₂Cl₂ / Ambient temperature

3: BF₃*Et₂O / 1,2-dichloro-ethane / 42 °C

4: NaCNBH₃ / 2-methyl-butan-2-ol / Ambient temperature

5: 90 percent / mCPBA / CH₂Cl₂ / Ambient temperature

6: HCO₂H, Et₃N / methanol

7: tetrahydrofuran / Ambient temperature

8: PPTS / dimethylformamide

9: 2,6-lutidine / dimethylformamide / -10 °C

10: 89 percent / LiAlH₄ / tetrahydrofuran / -78 °C

11: 99 percent / toluene / -20 °C

12: pyridine / Ambient temperature

13: n-Bu₄NF / tetrahydrofuran / Ambient temperature

14: CrO₃, pyridine / Ambient temperature

15: K₂CO₃ / methanol / Ambient temperature

16: 80 percent / NaH / tetrahydrofuran / Ambient temperature

17: 99 percent / HF, anisole / Ambient temperature

18: DCC, Et₃N / dimethylformamide / Ambient temperature

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; lithium aluminium tetrahydride; formic acid; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tin(IV) chloride; sodium hydride; sodium cyanoborohydride; potassium carbonate; methoxybenzene; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; tert-Amyl alcohol; nitromethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a110

Reference yield:

endo-4-hydroxy-2-oxabicyclo<3.3.1>non-6-en-3-one (99440-81-0) → [(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (99440-90-1)

Guidance literature:

Multi-step reaction with 17 steps

1: 86 percent / CrO₃, pyridine / CH₂Cl₂ / Ambient temperature

2: BF₃*Et₂O / 1,2-dichloro-ethane / 42 °C

3: NaCNBH₃ / 2-methyl-butan-2-ol / Ambient temperature

4: 90 percent / mCPBA / CH₂Cl₂ / Ambient temperature

5: HCO₂H, Et₃N / methanol

6: tetrahydrofuran / Ambient temperature

7: PPTS / dimethylformamide

8: 2,6-lutidine / dimethylformamide / -10 °C

9: 89 percent / LiAlH₄ / tetrahydrofuran / -78 °C

10: 99 percent / toluene / -20 °C

11: pyridine / Ambient temperature

12: n-Bu₄NF / tetrahydrofuran / Ambient temperature

13: CrO₃, pyridine / Ambient temperature

14: K₂CO₃ / methanol / Ambient temperature

15: 80 percent / NaH / tetrahydrofuran / Ambient temperature

16: 99 percent / HF, anisole / Ambient temperature

17: DCC, Et₃N / dimethylformamide / Ambient temperature

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; lithium aluminium tetrahydride; formic acid; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium cyanoborohydride; potassium carbonate; methoxybenzene; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; tert-Amyl alcohol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a110

Reference yield:

N-((1R,6R,9R)-8-Oxo-3,7-dioxa-tricyclo[4.3.1.02,4]dec-9-yl)-C-p-tolyl-methanesulfonamide (126423-62-9,126574-82-1) → [(S)-1-((3S,4S,4aS,5S,6S)-5,6,8-Trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (99440-90-1)

Guidance literature:

Multi-step reaction with 13 steps

1: HCO₂H, Et₃N / methanol

2: tetrahydrofuran / Ambient temperature

3: PPTS / dimethylformamide

4: 2,6-lutidine / dimethylformamide / -10 °C

5: 89 percent / LiAlH₄ / tetrahydrofuran / -78 °C

6: 99 percent / toluene / -20 °C

7: pyridine / Ambient temperature

8: n-Bu₄NF / tetrahydrofuran / Ambient temperature

9: CrO₃, pyridine / Ambient temperature

10: K₂CO₃ / methanol / Ambient temperature

11: 80 percent / NaH / tetrahydrofuran / Ambient temperature

12: 99 percent / HF, anisole / Ambient temperature

13: DCC, Et₃N / dimethylformamide / Ambient temperature

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; lithium aluminium tetrahydride; formic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; methoxybenzene; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a110

upstream raw materials:

N-Cbz-Ala

(+/-)-actinobolyl amine hydrofluoride salt

Oxo-acetic acid cyclohex-3-enyl ester

endo-4-hydroxy-2-oxabicyclo<3.3.1>non-6-en-3-one

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