[(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane

Base Information

• Chemical Name: [(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane
• CAS No.: 708253-90-1
• Molecular Formula: C₁₈H₃₀N₄OSi
• Molecular Weight: 346.548
• Mol file: 708253-90-1.mol

Synonyms:[(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane

Chemical Property of [(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane

There total 9 articles about [(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane 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:

[(2R,4R)-1-benzyl-4-[tert-butyl(dimethyl)silyl]oxy-pyrrolidin-2-yl]methanol (635299-81-9) → [(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane (708253-90-1)

Guidance literature:

With tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at -78 ℃; for 4.5h;

Reference yield:

Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester (708253-89-8) → [(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane (708253-90-1)

Guidance literature:

With sodium azide;

DOI:10.1081/NCN-120022747

Reference yield:

(3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol (161564-09-6) → [(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane (708253-90-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: NaN₃ / dimethylformamide / 65 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.02.034

upstream raw materials:

Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester

(3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol

(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin

(2S,4R)-1-benzyl-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate

(S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester

benzyl (3S,5R)-3-(tert-butoxycarbonylamino)-5-[tert-butyl(dimethyl)silyl]oxy-piperidine-1-carboxylate

benzyl (3S)-3-(tert-butoxycarbonylamino)-5-oxo-piperidine-1-carboxylate