(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

Base Information

• Chemical Name: (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
• CAS No.: 217820-50-3
• Molecular Formula: C₄₁H₇₂O₁₁Si₂
• Molecular Weight: 797.187

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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:

(2S,4R,5S)-2-(4-Methoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethoxy)-4-vinyl-[1,3]dioxane-5-carbaldehyde (217820-14-9) → (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 (217820-50-3)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; 1H-imidazole; dmap; potassium hydroxide; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; thexylborane; dihydrogen peroxide; sodium hexamethyldisilazane; potassium hexamethylsilazane; In N,N-dimethyl-formamide;

DOI:10.1021/jo981749j

Reference yield:

<2-<<<(2S,4R,5S)-5-<(Z)-2-iodovinyl>-2-(p-methoxyphenyl)-4-vinyl-m-dioxan-5-yl>oxy>methoxy>ethyl>trimethylsilane (217820-15-0) → (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 (217820-50-3)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 1H-imidazole; dmap; potassium hydroxide; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; thexylborane; dihydrogen peroxide; potassium hexamethylsilazane; In N,N-dimethyl-formamide;

DOI:10.1021/jo981749j

Reference yield:

<2-<<<(2S,4aS,7S,7aR)-5-ethoxydihydro-7-(iodomethyl)-2-(p-methoxyphenyl)-4H-furo<3,4-d>-m-dioxin-4a(5H)-yl>oxy>methoxy>ethyl>trimethylsilane → (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 (217820-50-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / pyridine, zinc / aq. ethanol / 5 h / 80 - 90 °C

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

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

4: 1.) 18-crown-6, potassium hexamethyldisilazide / 1.) THF, toluene, -78 -> -30 deg C, 2.) THF, toluene, 2 h

5: 41 percent / pyridine, osmium tetraoxide / 2 h

6: 73 percent / imidazole, 4-(N,N-dimethylamino)pyridine / dimethylformamide / Ambient temperature

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

With pyridine; 1H-imidazole; dmap; potassium hydroxide; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; thexylborane; dihydrogen peroxide; sodium hexamethyldisilazane; potassium hexamethylsilazane; zinc; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo981749j

upstream raw materials:

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

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

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

(1S,2S,3R,4S)-3-(methoxymethoxy)-2-<(Z)-2-<(2S,4R,5S)-2-(p-methoxyphenyl)-5-<<2-(trimethylsilyl)ethoxy>methoxy>-4-vinyl-m-dioxan-5-yl>vinyl>-7,7-dimethyl-1-vinylbicyclo<2.2.1>heptan-2-ol

Downstream raw materials:

[(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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