(2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde

Base Information

Chemical Name:(2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde
CAS No.:217820-07-0
Molecular Formula:C₃₅H₄₂O₈
Molecular Weight:590.714
Hs Code.:

Synonyms:(2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde

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Chemical Property of (2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde

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Technology Process of (2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde

There total 21 articles about (2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde 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: 89.0%

: 217820-06-9
(1S,2R,5R,6S,7E)-6-<(2R,4S,5S)-5-(benzyloxy)-4-(2-hydroxyethyl)-2-phenyl-m-dioxan-5-yl>-2-(methoxymethoxy)-5,11,11-trimethylbicyclo-<6.2.1>undec-7-ene-3,4-dione

: 217820-07-0
(2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1021/jo981749j

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 217820-07-0
(2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde

Guidance literature:: Multi-step reaction with 18 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

16: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂

17: 85 percent / hydrogen fluoride-pyridine / acetonitrile / 0.25 h / 0 °C

18: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

With 1H-imidazole; Oxone; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; cerium(III) chloride; oxalyl dichloride; 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; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo981749j

Reference yield:

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

: 217820-07-0
(2R,4S,5S)-5-(benzyloxy)-4-<(1E,3S,4R,7R,8S)-7-(methoxymethoxy)-4,11,11-trimethyl-5,6-dioxobicyclo-<6.2.1>undec-1-en-3-yl>-2-phenyl-m-dioxane-4-acetaldehyde

Guidance literature:: Multi-step reaction with 14 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

12: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂

13: 85 percent / hydrogen fluoride-pyridine / acetonitrile / 0.25 h / 0 °C

14: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

With Oxone; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; 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; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo981749j