(2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

Base Information

Chemical Name:(2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene
CAS No.:209251-03-6
Molecular Formula:C₂₇H₄₀O₃Si
Molecular Weight:440.698
Hs Code.:

Synonyms:(2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

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Chemical Property of (2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

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Technology Process of (2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

There total 5 articles about (2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene 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:

: 209251-06-9
(2R,3S,4R)-1-(tert-butyldiphenylsilanyloxy)-2,4-dimethyl-3-hydroxy-5-hexene

: 209251-03-6
(2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridine; ozone; dimethylsulfide / methanol; CH₂Cl₂ / -78 - 23 °C

2.1: i-Pr₂NEt; molecular sieves 4 Angstroem / CH₂Cl₂ / 72 h / 0 °C

2.2: aqueous HCl / 0.25 h

2.3: aqueous NaOH / tetrahydrofuran / 1 h

With pyridine; dimethylsulfide; 4 A molecular sieve; ozone; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
DOI:10.1021/jo0267908

Reference yield:

: (2R,3R,4S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

: 209251-03-6
(2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaIO₄ / tetrahydrofuran; H₂O / 23 °C

2.1: i-Pr₂NEt; molecular sieves 4 Angstroem / CH₂Cl₂ / 72 h / 0 °C

2.2: aqueous HCl / 0.25 h

2.3: aqueous NaOH / tetrahydrofuran / 1 h

With sodium periodate; 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo0267908

Reference yield:

: 51676-18-7
(Z)-crotyltrifluorosilane

: 209250-94-2
(2S,3R,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanal

: 209251-03-6
(2R,3R,4R,5R,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

: 209251-04-7
(2R,3R,4R,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

: (2R,3R,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-oct-7-ene-3,5-diol

Guidance literature:: (Z)-crotyltrifluorosilane; (2S,3R,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanal; With 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 72h;

With hydrogenchloride; for 0.25h;

With sodium hydroxide; In tetrahydrofuran; for 1h; Further stages.;
DOI:10.1021/jo0267908