(2S,3S,4R)-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxypiperidine

Base Information

Chemical Name:(2S,3S,4R)-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxypiperidine
CAS No.:865996-20-9
Molecular Formula:C₁₉H₃₁NO₅Si
Molecular Weight:381.544
Hs Code.:

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

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

Chemical Property:

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

There total 6 articles about (2S,3S,4R)-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2,3-dihydroxypiperidine 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:

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

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

Guidance literature:: Multi-step reaction with 4 steps

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

2: imidazole / dimethylformamide / 0 - 20 °C

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

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

With 1H-imidazole; osmium(VIII) oxide; 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 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

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

Guidance literature:: Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 0 - 20 °C

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

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

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

Reference yield:

: 865996-18-5
(4R)-1-N-(benzyloxycarbonyl)-3-bromo-4-(tert-butyldimethylsilyloxy)-1,4,5,6-tetrahydropyridine

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; In water; acetone; toluene; acetonitrile;
DOI:10.1021/jo051117e