(2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-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,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:566898-44-0
Molecular Formula:C₄₁H₅₇NO₈S
Molecular Weight:723.971
Hs Code.:

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

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

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

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Technology Process of (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-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,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-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: 26.0%

: 98-88-4
benzoyl chloride

: 168610-13-7
1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate

: 566898-21-3
(1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

: 566898-44-0
(2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: 1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate; (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan; With n-butyllithium; In 1,2-dimethoxyethane; hexane; at -78 - 0 ℃; for 3.5h;

benzoyl chloride; In 1,2-dimethoxyethane; hexane; at -78 - 20 ℃; for 0.5h;
DOI:10.1016/S0968-0896(02)00665-X

Reference yield:

: 26553-46-8
ethyl (E)-3-hexenoate

: 566898-44-0
(2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 15 percent / LiClO₄; 4,4'-thiobis(6-tert-butyl-m-cresol) / diethyl ether / 72 h / 20 °C

2.1: 74 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / 20 °C / 760 Torr

3.1: 93 percent / LiN(TMS)2 / tetrahydrofuran / 5 h / -70 - -40 °C

4.1: 72 percent / DBU / toluene / 3 h / 80 °C

5.1: 91 percent / H₂ / PtO₂ / ethanol / 4 h / 20 °C / 760 Torr

6.1: 87 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

7.1: 873 mg / BF₃*OEt₂ / CH₂Cl₂ / 16 h / -70 - 20 °C

8.1: 89 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

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

9.2: 100 percent / diethyl ether; toluene / 14 h / 0 - 20 °C

10.1: BH₃*THF / tetrahydrofuran / 10 h / -78 - 20 °C

10.2: 70 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11.1: 93 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

12.1: 279 mg / t-BuOK / dimethylsulfoxide / 14 h / 20 °C

13.1: 100 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

14.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 3.5 h / -78 - 0 °C

14.2: 26 percent / 1,2-dimethoxy-ethane; hexane / 0.5 h / -78 - 20 °C

With Santonox R; 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 / 15.1: Julia-Lythgoe coupling reaction;
DOI:10.1016/S0968-0896(02)00665-X

Reference yield:

: 2407-43-4,76291-90-2,92843-41-9,109668-80-6
(5S)-5-ethylfuran-2(5H)-one

: 566898-44-0
(2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 15 percent / LiClO₄; 4,4'-thiobis(6-tert-butyl-m-cresol) / diethyl ether / 72 h / 20 °C

2.1: 74 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / 20 °C / 760 Torr

3.1: 93 percent / LiN(TMS)2 / tetrahydrofuran / 5 h / -70 - -40 °C

4.1: 72 percent / DBU / toluene / 3 h / 80 °C

5.1: 91 percent / H₂ / PtO₂ / ethanol / 4 h / 20 °C / 760 Torr

6.1: 87 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

7.1: 873 mg / BF₃*OEt₂ / CH₂Cl₂ / 16 h / -70 - 20 °C

8.1: 89 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

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

9.2: 100 percent / diethyl ether; toluene / 14 h / 0 - 20 °C

10.1: BH₃*THF / tetrahydrofuran / 10 h / -78 - 20 °C

10.2: 70 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11.1: 93 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

12.1: 279 mg / t-BuOK / dimethylsulfoxide / 14 h / 20 °C

13.1: 100 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

14.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 3.5 h / -78 - 0 °C

14.2: 26 percent / 1,2-dimethoxy-ethane; hexane / 0.5 h / -78 - 20 °C

With Santonox R; 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 / 14.1: Julia-Lythgoe coupling reaction;
DOI:10.1016/S0968-0896(02)00665-X