[(S)-1-((3S,4R,4aR,5R,6R)-3-Dichloromethyl-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,4R,4aR,5R,6R)-3-Dichloromethyl-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.: 115559-70-1
• Molecular Formula: C₂₂H₂₆Cl₂N₂O₈
• Molecular Weight: 517.363

Synonyms:[(S)-1-((3S,4R,4aR,5R,6R)-3-Dichloromethyl-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,4R,4aR,5R,6R)-3-Dichloromethyl-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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-1-((3S,4R,4aR,5R,6R)-3-Dichloromethyl-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 18 articles about [(S)-1-((3S,4R,4aR,5R,6R)-3-Dichloromethyl-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: 30.0%

N-Cbz-Ala (1142-20-7) + (3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one (78013-07-7,79131-71-8,115649-44-0) → [(S)-1-((3S,4R,4aR,5R,6R)-3-Dichloromethyl-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (115559-70-1) + [(S)-1-((3R,4S,4aS,5S,6S)-3-Dichloromethyl-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (115534-44-6)

Guidance literature:

With triethylamine; dicyclohexyl-carbodiimide; In toluene;

DOI:10.1021/jo00252a060

Reference yield:

endo-(+/-)-N-(3-oxo-2-oxabicyclo<3.3.1>non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide (115534-35-5) → [(S)-1-((3S,4R,4aR,5R,6R)-3-Dichloromethyl-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (115559-70-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / mCPBA / CH₂Cl₂

2: HCOOH, MeOH, Et₃N

3: tetrahydrofuran

4: p-TsOH / dimethylformamide

5: 2,6-lutidine / dimethylformamide / -15 °C

6: 2.) n-Bu₄NF / 1.) THF, 2.) RT

7: CeCl₃ / diethyl ether / -100 °C

8: 90 percent / CrO₃, pyr / CH₂Cl₂

9: 80 percent / Et₃N, 4-pyrrolidinopyridine

10: 70 percent / NaOMe / methanol

11: 1.) n-Bu₄NF, 2.) HCl / 1.) THF, 52 deg C, 2.) MeOH

12: 30 percent / DCC, Et₃N / toluene

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; methanol; formic acid; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium methylate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00252a060

Reference yield:

(S)-N-Methoxy-N-methyl-2-((1S,2S,3S,5S)-2,3,5-trihydroxy-cyclohexyl)-2-(2-trimethylsilanyl-ethanesulfonylamino)-acetamide (126423-75-4) → [(S)-1-((3S,4R,4aR,5R,6R)-3-Dichloromethyl-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester (115559-70-1)

Guidance literature:

Multi-step reaction with 9 steps

1: p-TsOH / dimethylformamide

2: 2,6-lutidine / dimethylformamide / -15 °C

3: 2.) n-Bu₄NF / 1.) THF, 2.) RT

4: CeCl₃ / diethyl ether / -100 °C

5: 90 percent / CrO₃, pyr / CH₂Cl₂

6: 80 percent / Et₃N, 4-pyrrolidinopyridine

7: 70 percent / NaOMe / methanol

8: 1.) n-Bu₄NF, 2.) HCl / 1.) THF, 52 deg C, 2.) MeOH

9: 30 percent / DCC, Et₃N / toluene

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium methylate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00252a060

upstream raw materials:

N-Cbz-Ala

(3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one

endo-(+/-)-N-(3-oxo-2-oxabicyclo<3.3.1>non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide

2-Trimethylsilanyl-ethanesulfonic acid ((1R,6R,9R)-8-oxo-3,7-dioxa-tricyclo[4.3.1.0^2,4]dec-9-yl)-amide

Downstream raw materials:

(-)-Bactobolin

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