12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one

Base Information

Chemical Name:12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one
CAS No.:386761-69-9
Molecular Formula:C₃₄H₅₃NO₃Si
Molecular Weight:551.885
Hs Code.:

Synonyms:12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one

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Chemical Property of 12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one

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Technology Process of 12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one

There total 8 articles about 12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-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: 60.0%

: 386761-68-8
12-((2S,5R,6S)-5-(benzyloxy)-1-[(benzyloxy)carbonyl]-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)dodec-10-en-3-one

: 386761-69-9
12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one

Guidance literature:: With hydrogenchloride; hydrogen; palladium on activated charcoal; In methanol;
DOI:10.1055/s-2001-17461

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 386761-69-9
12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

2: 98 percent / DMAP; pyridine / 2.5 h / 0 - 20 °C

3: 89 percent / PPh₃ / tetrahydrofuran; H₂O / 12 h / 50 °C

4: 88 percent / Et₃N / methanol / 8 h / Heating

5: 100 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 20 °C

6: 58 percent / [1,3-(2,4,6-Me₃C₆H₃)2-imidazolidin-2-yl]Ru(PCy₃)Cl₂(=CHPh) / CH₂Cl₂ / 4 h / 50 °C

7: 60 percent / H₂; HCl / 10percent Pd/C / methanol / 20 h / 20 °C / 760.05 Torr

With pyridine; 1H-imidazole; hydrogenchloride; dmap; hydrogen; sodium carbonate; triethylamine; triphenylphosphine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo010653d

Reference yield:

: 386761-63-3
(2R,3R,6S)-6-azido-3-(benzyloxy)-1-[(tert-butyldiphenylsilyl)oxy]non-8-ene-2-ol

: 386761-69-9
12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / DMAP; pyridine / 2.5 h / 0 - 20 °C

2: 89 percent / PPh₃ / tetrahydrofuran; H₂O / 12 h / 50 °C

3: 88 percent / Et₃N / methanol / 8 h / Heating

4: 100 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 20 °C

5: 58 percent / [1,3-(2,4,6-Me₃C₆H₃)2-imidazolidin-2-yl]Ru(PCy₃)Cl₂(=CHPh) / CH₂Cl₂ / 4 h / 50 °C

6: 60 percent / H₂; HCl / 10percent Pd/C / methanol / 20 h / 20 °C / 760.05 Torr

With pyridine; hydrogenchloride; dmap; hydrogen; sodium carbonate; triethylamine; triphenylphosphine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo010653d