(4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

Base Information

Chemical Name:(4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one
CAS No.:158498-00-1
Molecular Formula:C₁₉H₂₈O₅
Molecular Weight:336.428
Hs Code.:

Synonyms:(4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

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Chemical Property of (4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

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Technology Process of (4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

There total 20 articles about (4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-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: 96.0%

: 158497-99-5
[4R-[4α,5α,8α(R*)]]-8-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-methylethyl]-4-[(4-methoxyphenyl)methoxy]-5-methyl-2-oxocanone

: 158498-00-1
(4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/ja00091a082

Reference yield: 90.0%

: 1041782-37-9
C₂₅H₄₂O₅Si

: 158498-00-1
(4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1002/anie.200800554

Reference yield:

: (2S,3R)-3-(4-methoxybenzyloxy)-2-methylpent-4-en-1-ol

: 158498-00-1
(4R,5S,8S)-8-((R)-2-Hydroxy-1-methyl-ethyl)-4-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-one

Guidance literature:: Multi-step reaction with 17 steps

1: imidazole / CH₂Cl₂ / Ambient temperature

2: 1.) 9-BBN, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 65 deg C

3: Et₃N / CH₂Cl₂ / Ambient temperature

4: n-Bu₄NF / tetrahydrofuran / 3 h / 65 °C

5: Dess-Martin periodinane

6: t-BuOK / tetrahydrofuran / -78 °C

7: 90 percent / I₂, morpholine / benzene / 55 °C

8: CrCl₂, NiCl₂ / tetrahydrofuran / 4 h / Ambient temperature

9: H₂ / Pd(CaCO₃, Pb) / benzene / 760 Torr / Ambient temperature

10: DMAP, pyridine / Ambient temperature

11: PPTS / CH₂Cl₂; methanol / Ambient temperature

12: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

13: NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature

14: 87 percent / methanolic K₂CO₃ / Ambient temperature

15: H₂ / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature

16: 1.) 2,2'-pyridine disulfide, PPh₃, 2.) AgBF₄ / 1.) CH₂Cl₂, RT, 2.) PhMe, 110 deg C

17: 96 percent / n-Bu₄NF, AcOH / tetrahydrofuran / 0 °C

With morpholine; pyridine; 1H-imidazole; chromium dichloride; dmap; sodium hydroxide; sodium chlorite; silver tetrafluoroborate; 9-borabicyclo[3.3.1]nonane dimer; 2,2'-dipyridyldisulphide; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; acetic acid; triethylamine; triphenylphosphine; nickel dichloride; palladium on activated charcoal; palladium on calcium fluoride poisoned with lead; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; tert-butyl alcohol; benzene;
DOI:10.1021/ja00091a082