[(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

Base Information

Chemical Name:[(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde
CAS No.:217820-22-9
Molecular Formula:C₄₁H₇₀O₁₁Si₂
Molecular Weight:795.171
Hs Code.:

[(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

Synonyms:[(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

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Chemical Property of [(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

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Technology Process of [(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

There total 8 articles about [(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-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: 82.0%

: 217820-50-3
(1S,2R,4S,5S,7S,8S)-7-(tert-butyldimethylsiloxy)-8-hydroxy-5-<(2S,4R,5S)-4-(2-hydroxyethyl)-2-(p-methoxyphenyl)-5-<<2-(trimethylsilyl)ethoxy>methoxy>-m-dioxan-5-yl>-2-(methoxymethoxy)-4,11,11-trimethylbicyclo<6.2.1>undecan-3-one

: 217820-22-9
[(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 1h;
DOI:10.1021/jo981749j

Reference yield:

: 217820-14-9
(2S,4R,5S)-2-(4-Methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-4-vinyl-[1,3]dioxane-5-carbaldehyde

: 217820-22-9
[(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) sodium hexamethyldisilazide / 1.) THF, room temperature, 10 min, 2.) THF

2: 1.) n-butyllithium / 1.) ether, pentane, 5 min, 2.) ether, pentane, 20 min

3: 1.) 18-crown-6, potassium hexamethyldisilazide / 1.) THF, toluene, -78 -> -30 deg C, 2.) THF, toluene, 2 h

4: 41 percent / pyridine, osmium tetraoxide / 2 h

5: 73 percent / imidazole, 4-(N,N-dimethylamino)pyridine / dimethylformamide / Ambient temperature

6: 1.) thexylborane, 2.) KOH, H₂O₂ / 1.) THF, 0 deg C, 30 min, 2.) water, THF, 12 h

7: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With pyridine; 1H-imidazole; dmap; potassium hydroxide; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; thexylborane; dihydrogen peroxide; sodium hexamethyldisilazane; potassium hexamethylsilazane; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo981749j

Reference yield:

: 217820-15-0
<2-<<<(2S,4R,5S)-5-<(Z)-2-iodovinyl>-2-(p-methoxyphenyl)-4-vinyl-m-dioxan-5-yl>oxy>methoxy>ethyl>trimethylsilane

: 217820-22-9
[(2S,4R,5S)-5-[(1S,2S,4S,5S,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2-(4-methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]dioxan-4-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-butyllithium / 1.) ether, pentane, 5 min, 2.) ether, pentane, 20 min

2: 1.) 18-crown-6, potassium hexamethyldisilazide / 1.) THF, toluene, -78 -> -30 deg C, 2.) THF, toluene, 2 h

3: 41 percent / pyridine, osmium tetraoxide / 2 h

4: 73 percent / imidazole, 4-(N,N-dimethylamino)pyridine / dimethylformamide / Ambient temperature

5: 1.) thexylborane, 2.) KOH, H₂O₂ / 1.) THF, 0 deg C, 30 min, 2.) water, THF, 12 h

6: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With pyridine; 1H-imidazole; dmap; potassium hydroxide; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; thexylborane; dihydrogen peroxide; potassium hexamethylsilazane; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo981749j