tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate
CAS No.:848668-36-0
Molecular Formula:C₃₄H₄₃NO₇Si
Molecular Weight:605.803
Hs Code.:

Synonyms:tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate

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Chemical Property of tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate

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Technology Process of tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate

There total 6 articles about tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate 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: 92.0%

: 848668-35-9
tert-butyl (5R,6R)-5-(benzoyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

: 848668-36-0
tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate

Guidance literature:: With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2004.12.001

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 848668-36-0
tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 3.96 g / NaHCO₃ / H₂O; tetrahydrofuran / 2 h / 20 °C

2: 98 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran; dimethylformamide; toluene / 5.5 h / 0 - 20 °C

3: 96 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 9 h / 20 °C

4: 92 percent / N-methylmorpholine N-oxide / osmium tetroxide / acetone; H₂O / 12 h / 20 °C

With potassium hexamethylsilazane; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; osmium(VIII) oxide; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.tet.2004.12.001

Reference yield:

: (4R,5R)-4-((tert-butyldiphenylsilyloxy)methyl)-2-phenyl-5-vinyl-4,5-dihydrooxazole

: 848668-36-0
tert-butyl (2R,3S,4S,5S)-3-(benzoyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: aq. HCl / tetrahydrofuran / 16 h / 20 °C

2: 3.96 g / NaHCO₃ / H₂O; tetrahydrofuran / 2 h / 20 °C

3: 98 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran; dimethylformamide; toluene / 5.5 h / 0 - 20 °C

4: 96 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 9 h / 20 °C

5: 92 percent / N-methylmorpholine N-oxide / osmium tetroxide / acetone; H₂O / 12 h / 20 °C

With hydrogenchloride; potassium hexamethylsilazane; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; osmium(VIII) oxide; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.tet.2004.12.001