(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

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Chemical Name:(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one
CAS No.:217820-04-7
Molecular Formula:C₄₁H₆₀O₈Si
Molecular Weight:709.008
Hs Code.:

(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

Synonyms:(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

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Chemical Property of (1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

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Technology Process of (1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

There total 18 articles about (1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-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: 72.0%

: 217820-03-6
(1S,2S,3R,4S)-1-<(E)-2-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>vinyl>-3-(methoxymethoxy)-7,7-dimethyl-2-<(E)-1-propenyl>bicyclo<2.2.1>heptan-2-ol

: 217820-04-7
(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

Guidance literature:: With 18-crown-6 ether; oxygen; potassium hexamethylsilazane; triphenylphosphine; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/jo981749j

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 217820-04-7
(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

Guidance literature:: Multi-step reaction with 15 steps

1: 78 percent / TsOH / dimethylformamide / Ambient temperature

2: NaHCO₃, sodium periodate / H₂O; CH₂Cl₂ / 0.5 h / Ambient temperature

3: 1.) potassium hexamethyldisilazide / 1.) THF, toluene, 0 deg C, 1 h, 2.) THF, toluene

4: 1.) 9-borabicyclo<3.3.1>nonane, 2.) sodium hydroxide, hydrogen peroxide / 1.) THF, 0 -> 20 deg C, 2.) THF, water, 0 -> 20 deg C

5: 87 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

6: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

7: 1.) n-butyllithium, 2.) cerium(III) chloride / 1.) THF, hexanes, -78 deg C, 1 h, 2.) THF, hexanes, -78 -> 20 deg C, overnight

8: 76 percent / Red-Al / tetrahydrofuran; toluene / 0 - 20 °C

9: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

10: 1.) potassium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 -> 20 deg C

11: 1.) lithium diisopropylamide / 1.) THF, hexanes, -78 deg C, 1 h, 2.) THF, hexanes

12: 1.) 18-crown-6, NaHCO₃, oxone, 2.) tetrabutylammonium fluoride / 1.) water, acetone, CH₂Cl₂, 1 h, 2.) THF, 0 deg C, 1 h

13: 79 percent / diisopropylethylamine / CH₂Cl₂

14: 1.) tert-butyllithium / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 30 min

15: 72 percent / 18-crown-6, oxygen, triphenylphosphine, potassium hexamethyldisilazide / tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; Oxone; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; oxygen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo981749j

Reference yield:

: 86023-73-6,6004-71-3
7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbaldehyde

: 217820-04-7
(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-<2-(tert-butyldimethylsiloxy)ethyl>-2-phenyl-m-dioxan-5-yl>-4-hydroxy-2-(methoxymethoxy)-5,11,11-trimethylbicyclo<6.2.1>undec-7-en-3-one

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) triphenylphosphine / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, 0 deg C, 10 min

2: 79 percent / sodium borohydride / methanol / 0 - 20 °C

3: 1.) n-butyllithium, 2.) cerium(III) chloride / 1.) THF, hexanes, -78 deg C, 1 h, 2.) THF, hexanes, -78 -> 20 deg C, overnight

4: 76 percent / Red-Al / tetrahydrofuran; toluene / 0 - 20 °C

5: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) potassium hydride, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 -> 20 deg C

7: 1.) lithium diisopropylamide / 1.) THF, hexanes, -78 deg C, 1 h, 2.) THF, hexanes

8: 1.) 18-crown-6, NaHCO₃, oxone, 2.) tetrabutylammonium fluoride / 1.) water, acetone, CH₂Cl₂, 1 h, 2.) THF, 0 deg C, 1 h

9: 79 percent / diisopropylethylamine / CH₂Cl₂

10: 1.) tert-butyllithium / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 30 min

11: 72 percent / 18-crown-6, oxygen, triphenylphosphine, potassium hexamethyldisilazide / tetrahydrofuran / -78 - 20 °C

With Oxone; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/jo981749j