(-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide

Base Information

Chemical Name:(-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide
CAS No.:175464-23-0
Molecular Formula:C₁₅H₁₆INO₄S
Molecular Weight:433.267
Hs Code.:

Synonyms:(-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide

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Chemical Property of (-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide

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Technology Process of (-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide

There total 1 articles about (-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide 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: 95.0%

: 98-59-9
p-toluenesulfonyl chloride

: (+)-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-3aβ,6aβ-cyclopenta[b]furan-7S-amine 4-methylbenzenesulfonate

: 175464-23-0
(-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide

Guidance literature:: In pyridine; for 2h;
DOI:10.1016/S0040-4020(99)00680-8

Reference yield: 97.0%

: 175464-23-0
(-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide

: 175464-24-1
(-)-3R-[[(4-methylphenyl)sulfonyl]amino]bicyclo[2.2.1]hept-5-ene-2αR carboxylic acid

Guidance literature:: With zinc; In acetic acid; for 0.5h; Heating;
DOI:10.1016/S0040-4020(99)00680-8

Reference yield:

: 175464-23-0
(-)-N-(3aβ,6aβ-hexahydro-6β-iodo-2-oxo-3αR,5α-methano-2H-cyclopenta[b]furan-7S-yl)-4-methylbenzenesulfonamide

: 175670-09-4
(+)-N-(hexahydro-2,5β-methano-1H-3aS,3aα,6aα-cyclopenta[c]pyrrol-4α-yl)-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / Zn / acetic acid / 0.5 h / Heating

2.1: O₃ / ethyl acetate; methanol / -78 °C

2.2: NaBH₄ / 40 h / -78 - 20 °C

2.3: 100 percent / 2N HCl / methanol / 72 h / 20 °C

3.1: 72 percent / NH₃ / methanol / 4 h / 60 °C / 2585.74 Torr

4.1: 74 percent / BH₃ / tetrahydrofuran / 18 h / Heating

5.1: 100 percent / Et₃N / acetone; H₂O / 18 h / 20 °C

6.1: 357 mg / pyridine / 21 h / 0 °C

7.1: TFA / 0.25 h / 20 °C

8.1: (i-Pr)2NEt / acetonitrile / 96 h / 20 °C

With borane; ammonia; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; In tetrahydrofuran; pyridine; methanol; water; acetic acid; ethyl acetate; acetone; acetonitrile; 1.1: Ring cleavage / 2.1: ozonolysis / 2.2: Reduction / 2.3: acidification / 3.1: Ring cleavage / 4.1: Reduction / 5.1: Acylation / 6.1: Tosylation / 7.1: Hydrolysis / 8.1: Cyclization;
DOI:10.1016/S0040-4020(99)00680-8