(+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

Base Information

Chemical Name:(+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one
CAS No.:128503-15-1
Molecular Formula:C₁₂H₁₁BrO₂Se
Molecular Weight:346.082
Hs Code.:

Synonyms:(+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

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Chemical Property of (+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

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Technology Process of (+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

There total 1 articles about (+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-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: 81.0%

: 34837-55-3
Phenylselenyl bromide

: 94482-75-4
(-)-(1S,4S)-7-oxabicyclo<2.2.1>-hept-5-en-2-one

: 128503-15-1
(+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

Guidance literature:: In chloroform; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(01)88356-3

Reference yield:

: 128503-15-1
(+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

: 128503-19-5
(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / mCPBA / CH₂Cl₂ / a) -78 deg C, b) 20 deg C, 5 h

2: 95 percent / NaBH₄ / methanol / 1 h / 0 °C

3: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 2) 20 deg C, 4 h

4: 99 percent / NaHCO₃, OsO₄, 30percent H₂O₂ / tetrahydrofuran; CCl₄ / 2 h / 0 °C

5: 94 percent / DMAP, pyridine / 12 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane;
DOI:10.1016/S0040-4020(01)88356-3

Reference yield:

: 128503-15-1,147127-91-1
(+/-)-(1RS,4SR,5SR,6SR)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

: 128503-18-4,146503-23-3
(+/-)-(1RS,3SR,4SR,6SR)-6-endo-benzyloxy-3-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: mCPBA / CH₂Cl₂ / a) -78 deg C, b) 20 deg C, 5 h

2: NaBH₄ / methanol / 1 h / 0 °C

3: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 2) 20 deg C, 4 h

4: NaHCO₃, OsO₄, 30percent H₂O₂ / tetrahydrofuran; CCl₄ / 2 h / 0 °C

With sodium tetrahydroborate; osmium(VIII) oxide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane;
DOI:10.1016/S0040-4020(01)88356-3