6-Oxabicyclo[3.2.1]octane-2,7-dione, 8,8-dimethyl-, (1R)-

Base Information

Chemical Name:6-Oxabicyclo[3.2.1]octane-2,7-dione, 8,8-dimethyl-, (1R)-
CAS No.:105996-77-8
Molecular Formula:C9H12O3
Molecular Weight:168.192
Hs Code.:

Synonyms:

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Chemical Property of 6-Oxabicyclo[3.2.1]octane-2,7-dione, 8,8-dimethyl-, (1R)-

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

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Technology Process of 6-Oxabicyclo[3.2.1]octane-2,7-dione, 8,8-dimethyl-, (1R)-

There total 1 articles about 6-Oxabicyclo[3.2.1]octane-2,7-dione, 8,8-dimethyl-, (1R)- 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:

: 562-13-0
2,2-dimethyl-1,3-cyclohexanedione

: 105996-77-8
(1R,5R)-(-)-8,8-dimethyl-6-oxabicyclo<3.2.1>octane-2,7-dione

Guidance literature:: Multi-step reaction with 14 steps

1: 79 percent / H₂O / 48 h / 30 °C / fermentation, baker's yeast

2: p-TsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 1.) NaOMe / 1.)THF, benzene, 10 min, 6 deg C 2.) RT, overnight

4: 6.9 g / p-TsOH / benzene / 3.5 h / Heating

5: p-TsOH / CH₂Cl₂ / Ambient temperature

6: 19.5 g / NaBH₄ / tetrahydrofuran; ethanol / 1.5 h / 0 - 4 °C

7: 14.1 g / CdCO₃, HgCl₂ / aq. ethanol / 0.03 h / Heating

8: 66 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 1 h / 0 - 5 °C

9: 1.) (n-Bu)3SnCH₂I 2.) n-BuLi / 1.) THF,DMF,44 h, RT 2.) THF, n-hexane, 1 h -65 deg C

10: pyridine / Ambient temperature

11: 95.7 percent / pTsOH / methanol / 1.33 h / Ambient temperature

12: 90.7 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 60 h / Ambient temperature

13: 86.8 percent / NaOMe / methanol / 24 h / Ambient temperature

14: 53.4 percent / RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.) 24 h, RT 2.) 48 h, 40 deg C

With dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; n-butyllithium; cadmium(II) carbonate; sodium methylate; tri-n-butylstannylmethyl iodide; toluene-4-sulfonic acid; mercury dichloride; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; ethanol; dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)91348-1

Reference yield:

: 105996-77-8
(1R,5R)-(-)-8,8-dimethyl-6-oxabicyclo<3.2.1>octane-2,7-dione

: 171231-07-5
(1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / t-BuOK / toluene / 2 h / 20 °C

2: 95 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

With lithium aluminium tetrahydride; potassium tert-butylate; In diethyl ether; toluene; 1: Substitution / 2: Ring cleavage;
DOI:10.1016/S0040-4020(00)00645-1

Reference yield:

: 105996-77-8
(1R,5R)-(-)-8,8-dimethyl-6-oxabicyclo<3.2.1>octane-2,7-dione

: C₂₃H₄₅BrO₃Si

Guidance literature:: Multi-step reaction with 9 steps

1.1: cerium(III) chloride heptahydrate / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere

1.2: 12 h / -78 - 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h / 0 - 20 °C

3.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; tetrabutyl-ammonium chloride; sodium hypochlorite; potassium bromide / dichloromethane; water / 0 - 20 °C

5.1: toluene / 48 h / 130 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 0 °C

7.1: triethylamine / dichloromethane / 3 h / -20 - 20 °C

8.1: tetrahydrofuran / 0.25 h / -20 °C / Inert atmosphere

9.1: phosphorus tribromide / diethyl ether; pentane; pyridine / 0.5 h / 0 °C

With sodium hypochlorite; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; tetrabutyl-ammonium chloride; hydrogen; phosphorus tribromide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; potassium bromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; toluene; pentane; 5.1: |Wittig Olefination;
DOI:10.1021/jo402572b