(3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester

Base Information

Chemical Name:(3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester
CAS No.:681433-93-2
Molecular Formula:C₂₉H₅₈O₅Si₃
Molecular Weight:571.033
Hs Code.:

Synonyms:(3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester

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Chemical Property of (3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester

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Technology Process of (3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester

There total 11 articles about (3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester 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: 93.0%

: 681433-92-1
3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[(tert-butyldimethylsilyl)oxyethylidene]cyclohexanol

: 2916-76-9
methyl (trimethylsilyl)acetate

: 681433-93-2
(3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1016/j.bmc.2006.01.061

Reference yield:

: (2R,6R)-[4-benzyloxy-2,6-bis-[(tert-butyldimethylsilyl)oxy]cyclohexylidene]acetaldehyde

: 681433-93-2
(3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / sodium borohydride / ethanol / 1 h / 0 °C

2: 91 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

3: hydrogen / Pd/C / ethanol / 2.5 h / 20 °C

4: oxalyl chloride; triethylamine; dimethyl sulfoxide / CH₂Cl₂ / -78 - 20 °C

5: 93 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation;
DOI:10.1016/j.bmc.2006.01.061

Reference yield:

: (2R,6R)-[4-benzyloxy-2,6-bis-[(tert-butyldimethylsilyl)oxy]cyclohexylidene]acetonitrile

: 681433-93-2
(3R,5R)-[3,5-bis-[(tert-butyldimethylsilyl)oxy]-4-[2-(tert-butyldimethylsilyl)oxyethyl]cyclohexylidene]acetic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / diisobutylaluminum hydride / toluene / 1.5 h / -78 °C

2: 98 percent / sodium borohydride / ethanol / 1 h / 0 °C

3: 91 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

4: hydrogen / Pd/C / ethanol / 2.5 h / 20 °C

5: oxalyl chloride; triethylamine; dimethyl sulfoxide / CH₂Cl₂ / -78 - 20 °C

6: 93 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Swern oxidation;
DOI:10.1016/j.bmc.2006.01.061