(2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one

Base Information

• Chemical Name: (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one
• CAS No.: 1415730-29-8
• Molecular Formula: C₄₃H₈₂O₇Si₃
• Molecular Weight: 795.376

Synonyms:

Chemical Property of (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one

There total 17 articles about (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-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: 25.0%

(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one (1415730-26-5) + (2R,3S,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxy-2,4,6-trimethylhept-6-enal (1415730-27-6) → (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one (1415730-29-8) + (2S,4S,7S,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one (1415730-38-9)

Guidance literature:

(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

(2R,3S,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxy-2,4,6-trimethylhept-6-enal; In tetrahydrofuran; at -78 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tet.2012.10.008

Reference yield:

(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhex-1-yne (1415730-31-2) → (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one (1415730-29-8) + (2S,4S,7S,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one (1415730-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate; mercury(II) diacetate / tetrahydrofuran / 5 h / 45 °C / pH 7 / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 5 h / -78 °C / Inert atmosphere

With mercury(II) diacetate; pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/j.tet.2012.10.008

Reference yield:

(2R,3S,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-triethylsilyloxy-2,4,6-trimethylhept-6-en-1-ol (1415730-46-9) → (2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one (1415730-29-8) + (2S,4S,7S,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-9-triethylsilyloxy-7-hydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one (1415730-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 0 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 5 h / -78 °C / Inert atmosphere

With oxalyl dichloride; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2012.10.008

upstream raw materials:

(2S,3R)-3-(tert-butyldimethylsilyloxy)-2,4-dimethylpent-4-en-1-ol

(5S)-6-(4-methoxybenzyl)oxy-5-methyl-3-oxohex-1-yne

(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhex-1-yne

(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

Downstream raw materials:

(2S,4S,7R,8R,9S,10S,11R)-4,11-bis(tert-butyldimethylsilyloxy)-7,9-dihydroxy-1-(4-methoxybenzyl)oxy-2,8,10,12-tetramethyltridec-12-en-5-one

(2R,4R,5R,6S)-2-[(1S,3S)-1-(tert-butyldimethylsilyloxy)-4-(4-methoxyphenyl)oxy-3-methylbutanyl]-6-[(1S,2R)-2-(tert-butyldimethylsilyloxy)-1,3-dimethylbut-3-enyl]-2,4-dihydroxy-5-methyltetrahydro-2H-pyran

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