(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one

Base Information

Chemical Name:(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one
CAS No.:879880-47-4
Molecular Formula:C₂₁H₃₁NO₅SeSi
Molecular Weight:484.526
Hs Code.:

Synonyms:(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one

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Chemical Property of (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one

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Technology Process of (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one

There total 7 articles about (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one 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: 87.0%

: 879880-46-3
(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-hydroxy-ethyl)-cyclopenta[b]furan-2-one

: 51694-22-5
ortho-nitrophenyl selenocyanate

: 879880-47-4
(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one

Guidance literature:: With tributylphosphine; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1021/jo051916x

Reference yield:

: 879880-39-4
(1S,6R,7S)-7-[(tert-butyldimethylsilyl)oxy]bicyclo[4.3.0]non-3-en-9-one

: 879880-47-4
(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / (CH₃)3N(O)*2H₂O / OsO₄ / 2-methyl-propan-2-ol; acetonitrile; H₂O / 1 h / 20 °C

2: 95 percent / NaIO₄ / RuCl₃*xH₂O / acetonitrile; CCl₄; H₂O / 2.5 h / 20 °C

3: 91 percent / diethyl ether / 0.75 h / 20 °C

4: 73.5 percent / L-Selectride / tetrahydrofuran / -78 - -40 °C

5: 97 percent / LiOH / propan-2-ol; H₂O / 2.5 h / 20 °C

6: 93.5 percent / BH₃*THF / tetrahydrofuran / 0 - 20 °C

7: 87 percent / n-Bu₃P / tetrahydrofuran / 8 h / 20 °C

With lithium hydroxide; sodium periodate; borane-THF; trimethylamine-N-oxide; tributylphosphine; L-Selectride; ruthenium trichloride; osmium(VIII) oxide; In tetrahydrofuran; tetrachloromethane; diethyl ether; water; isopropyl alcohol; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo051916x

Reference yield:

: 879880-40-7
(3S,3aR,5R,6S,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-5,6-dihydroxy-octahydro-inden-1-one

: 879880-47-4
(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / NaIO₄ / RuCl₃*xH₂O / acetonitrile; CCl₄; H₂O / 2.5 h / 20 °C

2: 91 percent / diethyl ether / 0.75 h / 20 °C

3: 73.5 percent / L-Selectride / tetrahydrofuran / -78 - -40 °C

4: 97 percent / LiOH / propan-2-ol; H₂O / 2.5 h / 20 °C

5: 93.5 percent / BH₃*THF / tetrahydrofuran / 0 - 20 °C

6: 87 percent / n-Bu₃P / tetrahydrofuran / 8 h / 20 °C

With lithium hydroxide; sodium periodate; borane-THF; tributylphosphine; L-Selectride; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; diethyl ether; water; isopropyl alcohol; acetonitrile;
DOI:10.1021/jo051916x