(2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine

Base Information

Chemical Name:(2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine
CAS No.:865996-21-0
Molecular Formula:C₁₉H₃₀N₄O₄Si
Molecular Weight:406.557
Hs Code.:

Synonyms:(2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine

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Chemical Property of (2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine

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Technology Process of (2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine

There total 8 articles about (2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine 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: 96.0%

: 865996-20-9
(2S,3S,4R)-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxypiperidine

: 865996-21-0
(2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine

Guidance literature:: (2S,3S,4R)-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxypiperidine; With 1H-imidazole; thionyl chloride; In tetrahydrofuran; N,N-dimethyl-formamide; at -30 ℃; for 1h;

With sodium azide; In tetrahydrofuran; N,N-dimethyl-formamide; at -30 - 0 ℃; for 2h;
DOI:10.1021/jo051117e

Reference yield:

: 865996-16-3
1-N-(benzyloxycarbonyl)-3-bromo-4-oxo-1,4,5,6-tetrahydropyridine

: 865996-21-0
(2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: (S)-2-methyl-CBS-oxazaborolidine; catecholborane / CH₂Cl₂; CCl₄; toluene / 17 h / -78 °C

2.1: imidazole / dimethylformamide / 0 - 20 °C

3.1: tri-n-butyltin hydride; 2,2'-azo-bis(isobutyronitrile) / toluene / 14 h / Heating

4.1: osmium tetroxide; N-methylmorpholine N-oxide / acetonitrile; acetone; H₂O / 14 h / 20 °C

5.1: thionyl chloride; imidazole / tetrahydrofuran; dimethylformamide / 1 h / -30 °C

5.2: 96 percent / sodium azide / dimethylformamide; tetrahydrofuran / 2 h / -30 - 0 °C

With 1H-imidazole; osmium(VIII) oxide; thionyl chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/jo051117e

Reference yield:

: 865996-17-4
(4R)-1-N-(benzyloxycarbonyl)-3-bromo-4-hydroxy-1,4,5,6-tetrahydropyridine

: 865996-21-0
(2R,3R,4R)-2-azido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide / 0 - 20 °C

2.1: tri-n-butyltin hydride; 2,2'-azo-bis(isobutyronitrile) / toluene / 14 h / Heating

3.1: osmium tetroxide; N-methylmorpholine N-oxide / acetonitrile; acetone; H₂O / 14 h / 20 °C

4.1: thionyl chloride; imidazole / tetrahydrofuran; dimethylformamide / 1 h / -30 °C

4.2: 96 percent / sodium azide / dimethylformamide; tetrahydrofuran / 2 h / -30 - 0 °C

With 1H-imidazole; osmium(VIII) oxide; thionyl chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/jo051117e