(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

Base Information

Chemical Name:(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine
CAS No.:858614-93-4
Molecular Formula:C₂₇H₃₉NO₄Si
Molecular Weight:469.696
Hs Code.:

Synonyms:(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

Suppliers and Price of (3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

Chemical Property:

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Technology Process of (3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

There total 10 articles about (3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine 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: 71.0%

: 917-54-4
methyllithium

: 858614-87-6
(3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine

: 858614-93-4
(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

Guidance literature:: With boron trifluoride diethyl etherate; In diethyl ether; at -78 ℃; for 2h;
DOI:10.1021/jo050519j

Reference yield:

: 224779-27-5
tert-butyl 3-hydroxy-1,2,3,6-tetrahydropyridine-N-carboxylate

: 858614-93-4
(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

Guidance literature:: Multi-step reaction with 5 steps

1: 49 percent / Pseudomonas cepacia lipase/ceramics / various solvent(s) / 18 h / 40 °C

2: 98 percent / Pseudomonas cepacia lipase/ceramics; aq. phosphate buffer / acetone / 18 h / 40 °C / pH 7.0

3: 99 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

4: 72 percent / oxone; aq. Na₂EDTA; CF₃COCH₃ / NaHCO₃ / acetonitrile / 0 °C

5: 71 percent / BF₃*Et₂O; CuCN / diethyl ether / 2 h / -78 °C

With 1H-imidazole; dmap; Oxone; phosphate buffer; Pseudomonas cepacia lipase; 1,1,1-trifluoro-2-propanone; ceramics; boron trifluoride diethyl etherate; edetate disodium; sodium hydrogencarbonate; In diethyl ether; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo050519j

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 858614-93-4
(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 72 percent / oxone; aq. Na₂EDTA; CF₃COCH₃ / NaHCO₃ / acetonitrile / 0 °C

3: 71 percent / BF₃*Et₂O; CuCN / diethyl ether / 2 h / -78 °C

With 1H-imidazole; dmap; Oxone; 1,1,1-trifluoro-2-propanone; boron trifluoride diethyl etherate; edetate disodium; sodium hydrogencarbonate; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo050519j