(2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol

Base Information

• Chemical Name: (2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol
• CAS No.: 1185341-67-6
• Molecular Formula: C₃₂H₆₂O₆Si₂
• Molecular Weight: 599.012

Synonyms:(2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol

Chemical Property of (2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol

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Technology Process of (2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol

There total 2 articles about (2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol 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: 87.0%

1,7-bis-(tert-butyldimethylsilanyloxy)-3-hydroxy-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonan-5-one → (2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol (1185341-67-6)

Guidance literature:

1,7-bis-(tert-butyldimethylsilanyloxy)-3-hydroxy-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonan-5-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at -30 ℃; for 1.25h;

With lithium borohydride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

With dihydrogen peroxide; sodium hydroxide; In methanol; water; at 20 ℃; for 1h; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/ja9056163

Reference yield:

1,7-bis-(tert-butyldimethylsilanyloxy)-3-hydroxy-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonan-5-one → (2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol (1185341-67-6) + C32H62O6Si2

Guidance literature:

1,7-bis-(tert-butyldimethylsilanyloxy)-3-hydroxy-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonan-5-one; With diethyl methoxy borane;

With lithium borohydride; optical yield given as %de;

DOI:10.1021/jo100201f

Reference yield: 80.0%

(2S,3R,4S,5R,6S,7R)-1,7-bis-(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5-diol (1185341-67-6) + 2,2-dimethoxy-propane (77-76-9) → (4R,5S,6R)-4-[(1S,2R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-6-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-2,2,5-trimethyl-[1,3]dioxane (1180131-44-5)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 0.5h;

DOI:10.1021/ja9056163 DOI:10.1021/jo100201f

Downstream raw materials:

(4R,5S,6R)-4-[(1S,2R)-2-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-1-methylbutyl]-6-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-2,2,5-trimethyl-[1,3]dioxane

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