(2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate

Base Information

Chemical Name:(2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate
CAS No.:448961-11-3
Molecular Formula:C₃₄H₃₉NO₆S
Molecular Weight:589.753
Hs Code.:

Synonyms:(2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate

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Chemical Property of (2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate

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Technology Process of (2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate

There total 5 articles about (2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate 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: 72.0%

: 22037-28-1
3-bromofurane

: 174757-25-6
5-Oxo-cyclopent-1-enecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

: 448961-11-3
(2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate

Guidance literature:: 3-bromofurane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

With thien-2-yl(cyano)copper lithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

5-Oxo-cyclopent-1-enecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester; In tetrahydrofuran; hexane; benzene; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/jo025612b

Reference yield:

: 87420-26-6
(1R,2S,3R)-3-[N-Phenylsulfonyl-N-(3,5-dimethylphenyl)amino]bornan-2-ol

: 448961-11-3
(2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / DMAP / toluene / Heating

2.1: pyridine / CH₂Cl₂

3.1: H₂O₂

4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.2: lithium 2-thienylcyanocuprate / tetrahydrofuran; hexane / 1 h / -78 °C

4.3: 72 percent / tetrahydrofuran; benzene; hexane / 1 h / -78 °C

With pyridine; dmap; n-butyllithium; dihydrogen peroxide; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo025612b

Reference yield:

: 10472-24-9,265317-94-0
methyl 2-oxocyclopentane-1-carboxylate

: 448961-11-3
(2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / DMAP / toluene / Heating

2.1: pyridine / CH₂Cl₂

3.1: H₂O₂

4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.2: lithium 2-thienylcyanocuprate / tetrahydrofuran; hexane / 1 h / -78 °C

4.3: 72 percent / tetrahydrofuran; benzene; hexane / 1 h / -78 °C

With pyridine; dmap; n-butyllithium; dihydrogen peroxide; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo025612b