(3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine

Base Information

• Chemical Name: (3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine
• CAS No.: 1318128-51-6
• Molecular Formula: C₄₀H₄₂N₄OSi
• Molecular Weight: 622.885
• Mol file: 1318128-51-6.mol

Synonyms:(3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine

Chemical Property of (3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine

There total 4 articles about (3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine 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: 65.0%

((2S,4R)-4-(tert-butyldiphenylsilyloxy)-1-tritylpyrrolidin-2-yl)methanol (1318128-16-3) → (3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine (1318128-51-6)

Guidance literature:

With tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ol201769b

Reference yield:

(2S,4R)-methyl 4-(tert-butyldiphenylsilyloxy)-1-tritylpyrrolidine-2-carboxylate (1318129-49-5) → (3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine (1318128-51-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.17 h / 0 - 20 °C

1.2: 0 °C

2.1: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 0.5 h / 0 °C

With lithium aluminium tetrahydride; tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol201769b

Reference yield:

methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate (129430-93-9,129430-94-0) → (3R,5R)-3-azido-5-(tert-butyldiphenylsilyloxy)-1-tritylpiperidine (1318128-51-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.17 h / 0 - 20 °C

2.2: 0 °C

3.1: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 0.5 h / 0 °C

With dmap; lithium aluminium tetrahydride; tetrabutylammoniun azide; triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol201769b

upstream raw materials:

(2S,4R)-methyl 4-(tert-butyldiphenylsilyloxy)-1-tritylpyrrolidine-2-carboxylate

((2S,4R)-4-(tert-butyldiphenylsilyloxy)-1-tritylpyrrolidin-2-yl)methanol

methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate

tert-butylchlorodiphenylsilane

Refernces

• 1、 Cochi, Anne,Gomez Pardo, Domingo,Cossy, Janine. "Access to optically active 3-azido- and 3-aminopiperidine derivatives by enantioselective ring expansion of prolinols". . p. 4442 - 4445. Retrieved 2011/10/05.