(2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 503443-48-9
• Molecular Formula: C₄₀H₅₅NO₈S
• Molecular Weight: 709.945
• Mol file: 503443-48-9.mol

Synonyms:

Chemical Property of (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

There total 20 articles about (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl 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:

4,5,6,7-tetrahydroisobenzofuran-5-ol (129272-02-2) → (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (503443-48-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 84 percent / DBU / 2 h / 80 °C

3.1: 47 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / 0 - 10 °C / 760 Torr

4.1: 72 percent / lithium perchlorate / diethyl ether / 20 °C

5.1: 61 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / 760 Torr

6.1: 100 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C

7.1: 78 percent / DBU / toluene / 100 °C

8.1: 93 percent / H₂ / PtO₂ / ethanol / 20 °C / 760 Torr

9.1: BIBAL-H / diethyl ether; hexane / -78 °C

10.1: 0.89 g / BF₃*Et₂O / CH₂Cl₂ / -60 °C

11.1: 92 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

12.1: NaN(TMS)2 / diethyl ether; toluene / 20 °C

12.2: 88 percent / diethyl ether; toluene / 20 °C

13.1: BH₃*THF / tetrahydrofuran / -78 °C

13.2: 75 percent / aq. NaOH; H₂O₂ / 0 °C

14.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

15.1: t-BuOK / dimethylsulfoxide / 20 °C

16.1: 311 mg / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH₂Cl₂ / 20 °C

17.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / -78 °C

17.2: 1,2-dimethoxy-ethane; hexane / -78 °C

18.1: 1,2-dimethoxy-ethane; hexane / -20 °C

With dmap; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 4.1: Diels-Alder reaction / 12.2: Wittig reaction / 17.2: Julia-Lythgoe reaction;

DOI:10.1016/S0040-4020(02)01358-3

Reference yield:

4,5,6,7-tetrahydroisobenzofuran (91632-72-3) → (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (503443-48-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 72 percent / lithium perchlorate / diethyl ether / 20 °C

2.1: 61 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / 760 Torr

3.1: 100 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C

4.1: 78 percent / DBU / toluene / 100 °C

5.1: 93 percent / H₂ / PtO₂ / ethanol / 20 °C / 760 Torr

6.1: BIBAL-H / diethyl ether; hexane / -78 °C

7.1: 0.89 g / BF₃*Et₂O / CH₂Cl₂ / -60 °C

8.1: 92 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 20 °C

9.2: 88 percent / diethyl ether; toluene / 20 °C

10.1: BH₃*THF / tetrahydrofuran / -78 °C

10.2: 75 percent / aq. NaOH; H₂O₂ / 0 °C

11.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

12.1: t-BuOK / dimethylsulfoxide / 20 °C

13.1: 311 mg / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH₂Cl₂ / 20 °C

14.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / -78 °C

14.2: 1,2-dimethoxy-ethane; hexane / -78 °C

15.1: 1,2-dimethoxy-ethane; hexane / -20 °C

With dmap; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Diels-Alder reaction / 9.2: Wittig reaction / 14.2: Julia-Lythgoe reaction;

DOI:10.1016/S0040-4020(02)01358-3

Reference yield:

4,5-dihydroisobenzofuran (503443-47-8) → (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (503443-48-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 47 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / 0 - 10 °C / 760 Torr

2.1: 72 percent / lithium perchlorate / diethyl ether / 20 °C

3.1: 61 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / 760 Torr

4.1: 100 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C

5.1: 78 percent / DBU / toluene / 100 °C

6.1: 93 percent / H₂ / PtO₂ / ethanol / 20 °C / 760 Torr

7.1: BIBAL-H / diethyl ether; hexane / -78 °C

8.1: 0.89 g / BF₃*Et₂O / CH₂Cl₂ / -60 °C

9.1: 92 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

10.1: NaN(TMS)2 / diethyl ether; toluene / 20 °C

10.2: 88 percent / diethyl ether; toluene / 20 °C

11.1: BH₃*THF / tetrahydrofuran / -78 °C

11.2: 75 percent / aq. NaOH; H₂O₂ / 0 °C

12.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

13.1: t-BuOK / dimethylsulfoxide / 20 °C

14.1: 311 mg / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH₂Cl₂ / 20 °C

15.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / -78 °C

15.2: 1,2-dimethoxy-ethane; hexane / -78 °C

16.1: 1,2-dimethoxy-ethane; hexane / -20 °C

With dmap; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 2.1: Diels-Alder reaction / 10.2: Wittig reaction / 15.2: Julia-Lythgoe reaction;

DOI:10.1016/S0040-4020(02)01358-3

upstream raw materials:

benzoyl chloride

1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate

(1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-4-((phenylsulfonyl)methyl)dodecahydronaphtho[2,3-c]furan

4,5,6,7-tetrahydroisobenzofuran-5-ol