(3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester

Base Information

Chemical Name:(3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester
CAS No.:197016-10-7
Molecular Formula:C₂₈H₅₀O₆SSi
Molecular Weight:542.853
Hs Code.:

Synonyms:(3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester

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Chemical Property of (3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester

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Technology Process of (3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester

There total 12 articles about (3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic 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: 97.0%

: 197015-99-9
(3S,5R)-3,5-Dimethyl-6-oxo-hexanoic acid methyl ester

: 197016-00-5
(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone

: 197016-10-7
(3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃;
DOI:10.1002/anie.199717451

Reference yield:

: 873-55-2
sodium benzenesulfonate

: 197016-10-7
(3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / various solvent(s) / 130 °C

2: 91 percent / K₂CO₃, MeOH / 25 °C

3: 99 percent / imidazole, DMAP / dimethylformamide / 50 °C

4: 97 percent / BuLi / tetrahydrofuran / -78 °C

With 1H-imidazole; methanol; dmap; n-butyllithium; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/anie.199717451

Reference yield:

: 197016-03-8
(2S,4R)-2,4-dimethyl-5-(triisopropylsilyloxy)pentan-1-ol

: 197016-10-7
(3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N / CH₂Cl₂ / -40 °C

2: LiBr / tetrahydrofuran / 25 °C

3: 95 percent / dimethylsulfoxide / 25 °C

4: 84 percent / NaOH / ethanol / 80 °C

5: 90 percent / diethyl ether / 0 °C

6: PCC, SiO₂ / CH₂Cl₂

7: 97 percent / BuLi / tetrahydrofuran / -78 °C

With sodium hydroxide; n-butyllithium; silica gel; triethylamine; pyridinium chlorochromate; lithium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1002/anie.199717451