(3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine

Base Information

• Chemical Name: (3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine
• CAS No.: 1271240-73-3
• Molecular Formula: C₃₁H₃₆N₄O₅
• Molecular Weight: 544.651
• Mol file: 1271240-73-3.mol

Synonyms:(3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine

Chemical Property of (3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine

There total 10 articles about (3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine 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: 93.0%

(3R,5R)-N-tert-butyloxycarbonyl-5-dimethoxytrityloxy-3-mesyloxypiperidine → (3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine (1271240-73-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 12h;

DOI:10.1016/j.tet.2010.12.029

Reference yield:

(3R,5R)-1-N-tert-butyloxycarbonyl-3,5-dihydroxypiperidine (1271240-62-0) → (3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine (1271240-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 7 h / Inert atmosphere

2: dmap / dichloromethane / 1 h

3: sodium azide / N,N-dimethyl-formamide / 12 h / 90 °C

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

DOI:10.1016/j.tet.2010.12.029

Reference yield:

(3R,5R)-dihydroxypiperidine (1043449-04-2) → (3S,5R)-3-azido-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine (1271240-73-3)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate / ethanol; water / 2 h

2: pyridine / 7 h / Inert atmosphere

3: dmap / dichloromethane / 1 h

4: sodium azide / N,N-dimethyl-formamide / 12 h / 90 °C

With pyridine; dmap; sodium azide; sodium hydrogencarbonate; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2010.12.029

upstream raw materials:

(3R,5R)-dihydroxypiperidine

(3R,5R)-1-N-tert-butyloxycarbonyl-3,5-dihydroxypiperidine

(3R,5R)-5-dimethoxytrityloxy-1-N-tert-butyloxycarbonyl-3-hydroxypiperidine

di-tert-butyl dicarbonate

Downstream raw materials:

(3S,5R)-3-amino-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidine

1-((3S,5R)-3-amino-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidin-3-yl)-3-((E)-3-ethoxyacryloyl)urea

1-((3S,5R)-3-amino-1-N-tert-butyloxycarbonyl-5-dimethoxytrityloxypiperidin-3-yl)-3-((E)-3-ethoxy-2-methylacryloyl)urea