(3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine

Base Information

• Chemical Name: (3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine
• CAS No.: 858614-87-6
• Molecular Formula: C₂₆H₃₅NO₄Si
• Molecular Weight: 453.654
• Mol file: 858614-87-6.mol

Synonyms:(3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine

Chemical Property of (3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine

There total 12 articles about (3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine 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: 72.0%

t-butyl (3R)-3-[(t-butyldiphenylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate (804500-78-5) → (3S,4R,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine + (3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine (858614-87-6)

Guidance literature:

With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In acetonitrile; at 0 ℃;

DOI:10.1021/jo050519j

Reference yield:

tert-butyl 3-hydroxy-1,2,3,6-tetrahydropyridine-N-carboxylate (224779-27-5) → (3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine (858614-87-6)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; dmap; Oxone; phosphate buffer; Pseudomonas cepacia lipase; 1,1,1-trifluoro-2-propanone; ceramics; edetate disodium; sodium hydrogencarbonate; In dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo050519j

Reference yield:

tert-butyl (R)-3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate (780782-29-8) → (3S,4S,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4,5-epoxypiperidine (858614-87-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; dmap; Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In dichloromethane; acetonitrile;

DOI:10.1021/jo050519j

upstream raw materials:

t-butyl (3R)-3-[(t-butyldiphenylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate

di-tert-butyl dicarbonate

tert-butylchlorodiphenylsilane

tert-butyl 3-hydroxy-1,2,3,6-tetrahydropyridine-N-carboxylate

Downstream raw materials:

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

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

(3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)piperidine

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