(2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

Base Information

Chemical Name:(2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile
CAS No.:487065-49-6
Molecular Formula:C₁₉H₂₈N₂O₃
Molecular Weight:332.443
Hs Code.:

Synonyms:(2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

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Chemical Property of (2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

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Technology Process of (2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

There total 2 articles about (2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile 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: 44.0%

: 50587-77-4
2-(benzyl(tert-butyl)amino)acetonitrile

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: (2R,3R,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

: 487065-49-6
(2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; at -80 ℃;
DOI:10.1021/jo025872t

Reference yield:

: 3378-72-1
N-tert-butylbenzylamine

: 487065-49-6
(2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 79 percent / K₂CO₃; NaI / acetonitrile / 12 h / 20 °C

2: 44 percent / LDA / tetrahydrofuran; heptane / -80 °C

With potassium carbonate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; acetonitrile;
DOI:10.1021/jo025872t

Reference yield: 79.0%

: 487065-49-6
(2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile

: 6088-87-5,53247-17-9
2-butenylmagnesium bromide

: (1S,2S,3R)-3-Amino-2-(benzyl-tert-butyl-amino)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-hex-5-en-1-ol

Guidance literature:: (2S,3S,4R)-N-benzyl-N-tert-butyl-4,5-O-isopropylidene-2-amino-3,4,5-trihydroxyvaleronitrile; 2-butenylmagnesium bromide; In tetrahydrofuran; at 0 ℃;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 - 20 ℃; Further stages.;
DOI:10.1021/jo025872t