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  • 93
    Millipore myrtenol
    Synthesis of HU-433. Reagents and conditions were as follows: ( a ) (1 R <t>)-(-)-myrtenol</t> 95%, pivaloyl chloride, pyridine, 0 °C, then overnight at room temperature (r.t.), 91% isolated. ( b ) CrO 3 , CH 3 CN, 0 °C, then t -BuOOH, 1 h at r.t., 25% isolated. ( c ) EtOH, NaBH 4 , 4 h, 91% isolated. ( d ) CH 2 Cl 2, dry p-TSA, 5-(1,1-dimethylheptyl)resorcinol,1.5 h. at r.t., 43% isolated. ( e ) K 2 CO 3 , DMF, CH 3 I, overnight at r.t. 67% yield. ( f ) Et 2 O, LiAlH 4 , reflux, 80% isolated.
    Myrtenol, supplied by Millipore, used in various techniques. Bioz Stars score: 93/100, based on 33 PubMed citations. ZERO BIAS - scores, article reviews, protocol conditions and more
    https://www.bioz.com/result/myrtenol/product/Millipore
    Average 93 stars, based on 33 article reviews
    Price from $9.99 to $1999.99
    myrtenol - by Bioz Stars, 2020-08
    93/100 stars
      Buy from Supplier

    95
    Tocris hu 308 4 4 1 1 dimethylheptyl 2 6 dimethoxyphenyl 6 6 dimethylbicyclo 3 1 1 hept 2 ene 2 methanol
    Synthesis of HU-433. Reagents and conditions were as follows: ( a ) (1 R <t>)-(-)-myrtenol</t> 95%, pivaloyl chloride, pyridine, 0 °C, then overnight at room temperature (r.t.), 91% isolated. ( b ) CrO 3 , CH 3 CN, 0 °C, then t -BuOOH, 1 h at r.t., 25% isolated. ( c ) EtOH, NaBH 4 , 4 h, 91% isolated. ( d ) CH 2 Cl 2, dry p-TSA, 5-(1,1-dimethylheptyl)resorcinol,1.5 h. at r.t., 43% isolated. ( e ) K 2 CO 3 , DMF, CH 3 I, overnight at r.t. 67% yield. ( f ) Et 2 O, LiAlH 4 , reflux, 80% isolated.
    Hu 308 4 4 1 1 Dimethylheptyl 2 6 Dimethoxyphenyl 6 6 Dimethylbicyclo 3 1 1 Hept 2 Ene 2 Methanol, supplied by Tocris, used in various techniques. Bioz Stars score: 95/100, based on 2 PubMed citations. ZERO BIAS - scores, article reviews, protocol conditions and more
    https://www.bioz.com/result/hu 308 4 4 1 1 dimethylheptyl 2 6 dimethoxyphenyl 6 6 dimethylbicyclo 3 1 1 hept 2 ene 2 methanol/product/Tocris
    Average 95 stars, based on 2 article reviews
    Price from $9.99 to $1999.99
    hu 308 4 4 1 1 dimethylheptyl 2 6 dimethoxyphenyl 6 6 dimethylbicyclo 3 1 1 hept 2 ene 2 methanol - by Bioz Stars, 2020-08
    95/100 stars
      Buy from Supplier

    Image Search Results


    Synthesis of HU-433. Reagents and conditions were as follows: ( a ) (1 R )-(-)-myrtenol 95%, pivaloyl chloride, pyridine, 0 °C, then overnight at room temperature (r.t.), 91% isolated. ( b ) CrO 3 , CH 3 CN, 0 °C, then t -BuOOH, 1 h at r.t., 25% isolated. ( c ) EtOH, NaBH 4 , 4 h, 91% isolated. ( d ) CH 2 Cl 2, dry p-TSA, 5-(1,1-dimethylheptyl)resorcinol,1.5 h. at r.t., 43% isolated. ( e ) K 2 CO 3 , DMF, CH 3 I, overnight at r.t. 67% yield. ( f ) Et 2 O, LiAlH 4 , reflux, 80% isolated.

    Journal: Proceedings of the National Academy of Sciences of the United States of America

    Article Title: CB2 cannabinoid receptor agonist enantiomers HU-433 and HU-308: An inverse relationship between binding affinity and biological potency

    doi: 10.1073/pnas.1503395112

    Figure Lengend Snippet: Synthesis of HU-433. Reagents and conditions were as follows: ( a ) (1 R )-(-)-myrtenol 95%, pivaloyl chloride, pyridine, 0 °C, then overnight at room temperature (r.t.), 91% isolated. ( b ) CrO 3 , CH 3 CN, 0 °C, then t -BuOOH, 1 h at r.t., 25% isolated. ( c ) EtOH, NaBH 4 , 4 h, 91% isolated. ( d ) CH 2 Cl 2, dry p-TSA, 5-(1,1-dimethylheptyl)resorcinol,1.5 h. at r.t., 43% isolated. ( e ) K 2 CO 3 , DMF, CH 3 I, overnight at r.t. 67% yield. ( f ) Et 2 O, LiAlH 4 , reflux, 80% isolated.

    Article Snippet: Pivaloyl chloride (8 g, 67 mmol) was added slowly to a solution of myrtenol (commercial myrtenol; Aldrich; CAS 19894-97-4), [α]D = −51°) (5 g, 33 mmol) in dry pyridine (25 mL), with cooling in ice bath.

    Techniques: Isolation, Reflux