(2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3aS,4S,4aS,8aR,9aS)-1-methoxy-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-((1S,3aS,4S,4aS,8aR,9aS)-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 566898-37-1
• Molecular Formula: C₃₉H₅₃NO₈S
• Molecular Weight: 695.918

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

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

Chemical Property:

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

There total 16 articles about (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3aS,4S,4aS,8aR,9aS)-1-methoxy-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: 42.0%

benzoyl chloride (98-88-4) + 1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate (168610-13-7) + (1S,3aS,4S,4aS,8aR,9aS)-dodecahydro-1-methoxy-4-(phenylsulfonyl)methylnaphtho[2,3-c]furan (479195-80-7) → (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3aS,4S,4aS,8aR,9aS)-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (566898-37-1)

Guidance literature:

1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate; (1S,3aS,4S,4aS,8aR,9aS)-dodecahydro-1-methoxy-4-(phenylsulfonyl)methylnaphtho[2,3-c]furan; With n-butyllithium; In 1,2-dimethoxyethane; hexane; at -78 ℃; for 2.5h;

benzoyl chloride; In 1,2-dimethoxyethane; hexane; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(02)00665-X

Reference yield:

4,5,6,7-tetrahydroisobenzofuran (91632-72-3) → (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3aS,4S,4aS,8aR,9aS)-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (566898-37-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 49 percent / LiClO₄; 4,4'-thiobis(6-tert-butyl-m-cresol) / diethyl ether / 48 h / 20 °C

2.1: 98 percent / H₂ / 10 percent Pd/C / ethanol / 5 h / 20 °C / 760 Torr

3.1: 99 percent / LiN(TMS)2 / tetrahydrofuran / -70 - -40 °C

4.1: 70 percent / DBU / toluene / 4 h / 80 °C

5.1: 95 percent / H₂ / PtO₂ / ethanol / 2 h / 20 °C / 760 Torr

6.1: 85 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

7.1: 4.56 g / BF₃*OEt₂ / CH₂Cl₂ / -70 - 20 °C

8.1: 97 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1 h / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 0.5 h / 20 °C

9.2: 54 percent / dimethylsulfoxide; toluene / -78 - 20 °C

10.1: BH₃*THF / tetrahydrofuran / 7 h / 20 °C

10.2: 82 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11.1: 30 percent / Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

12.1: 100 percent / aq. NaOH / ethanol / 20 °C

13.1: 79 percent / (cyanomethyl)trimethylphosphonium iodide; iPr₂NEt / acetonitrile / 80 °C

14.1: 86 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 20 °C

15.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 2.5 h / -78 °C

15.2: 42 percent / 1,2-dimethoxy-ethane; hexane / 1 h / 20 °C

With sodium hydroxide; Santonox R; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; (cyanomethyl)trimethyl-phosphonium iodide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 1.1: Diels-Alder reaction / 9.2: Wittig reaction / 15.1: Julia-Lythgoe coupling reaction;

DOI:10.1016/S0968-0896(02)00665-X

Reference yield:

(+/-)-(3aR,4S,9R,9aR)-4,9-epoxy-3a,4,5,6,7,8,9,9a-octahydronaphtho[2,3-c]furan-1(3H)-one → (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3aS,4S,4aS,8aR,9aS)-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (566898-37-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 98 percent / H₂ / 10 percent Pd/C / ethanol / 5 h / 20 °C / 760 Torr

2.1: 99 percent / LiN(TMS)2 / tetrahydrofuran / -70 - -40 °C

3.1: 70 percent / DBU / toluene / 4 h / 80 °C

4.1: 95 percent / H₂ / PtO₂ / ethanol / 2 h / 20 °C / 760 Torr

5.1: 85 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

6.1: 4.56 g / BF₃*OEt₂ / CH₂Cl₂ / -70 - 20 °C

7.1: 97 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1 h / 20 °C

8.1: NaN(TMS)2 / diethyl ether; toluene / 0.5 h / 20 °C

8.2: 54 percent / dimethylsulfoxide; toluene / -78 - 20 °C

9.1: BH₃*THF / tetrahydrofuran / 7 h / 20 °C

9.2: 82 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

10.1: 30 percent / Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

11.1: 100 percent / aq. NaOH / ethanol / 20 °C

12.1: 79 percent / (cyanomethyl)trimethylphosphonium iodide; iPr₂NEt / acetonitrile / 80 °C

13.1: 86 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 20 °C

14.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 2.5 h / -78 °C

14.2: 42 percent / 1,2-dimethoxy-ethane; hexane / 1 h / 20 °C

With sodium hydroxide; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; (cyanomethyl)trimethyl-phosphonium iodide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 8.2: Wittig reaction / 14.1: Julia-Lythgoe coupling reaction;

DOI:10.1016/S0968-0896(02)00665-X

upstream raw materials:

benzoyl chloride

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

(1S,3aS,4S,4aS,8aR,9aS)-dodecahydro-1-methoxy-4-(phenylsulfonyl)methylnaphtho[2,3-c]furan

4,5,6,7-tetrahydroisobenzofuran

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