(2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine

Base Information

Chemical Name:(2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine
CAS No.:865996-22-1
Molecular Formula:C₂₁H₃₄N₂O₅Si
Molecular Weight:422.597
Hs Code.:

Synonyms:(2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine

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Chemical Property of (2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine

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Technology Process of (2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine

There total 10 articles about (2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine 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: 90.0%

: 108-24-7
acetic anhydride

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

: 865996-22-1
(2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine

Guidance literature:: With hydrogen; nickel; In ethanol; for 4h;
DOI:10.1021/jo051117e

Reference yield: 75.0%

: 220494-26-8
selenoacetic acid

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

: 865996-22-1
(2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine

Guidance literature:: With 2,6-dimethylpyridine; In chloroform; toluene; for 12h; Heating;
DOI:10.1021/ol047889z

Reference yield:

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

: 865996-22-1
(2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine

Guidance literature:: Multi-step reaction with 6 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

6.1: 90 percent / Raney nickel; hydrogen / ethanol / 4 h

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