(5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol

Base Information

• Chemical Name: (5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol
• CAS No.: 169736-72-5
• Molecular Formula: C₄₃H₇₆O₅Si₃
• Molecular Weight: 757.33

Synonyms:(5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol

Chemical Property of (5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol

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Technology Process of (5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol

There total 1 articles about (5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol 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:

3-methyl-butan-2-one (563-80-4) + (2R,3S,4S,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-3-triethylsilanyloxy-heptanal → (5R,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol + (5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol (169736-72-5)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; Product distribution; aldol reactions with various enolates, stereoselectivity is dependent on the metal, the aldehyde stereochemistry and the protecting group;

DOI:10.1016/0040-4039(95)00626-N

Reference yield: 59.0%

methanol (67-56-1) + (5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol (169736-72-5) → (2S,4S,5S,6R)-6-[(1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-2-isopropyl-2-methoxy-5-methyl-tetrahydro-pyran-4-ol

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 0 ℃; for 48h;

DOI:10.1021/jo0164148

Reference yield:

(5S,6S,7R,8S,9S,10R)-3-oxo-7-[(triethylsilyl)oxy]-9-[(tert-butyl-dimethylsilyl)oxy]-11-[(tert-butyl-diphenylsilyl)oxy]-2,6,8,10-tetramethyl-undecan-5-ol (169736-72-5) → Acetic acid (2S,4S,5S,6R)-6-[(1R,2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-2-isopropyl-2-methoxy-5-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / PPTs / CH₂Cl₂ / 48 h / 0 °C

2: 84 percent / pyridine / DMAP / CH₂Cl₂ / 17 h

With pyridine; pyridinium p-toluenesulfonate; dmap; In dichloromethane;

DOI:10.1021/jo0164148

upstream raw materials:

3-methyl-butan-2-one

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