(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

Base Information

Chemical Name:(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine
CAS No.:888323-23-7
Molecular Formula:C₄₂H₆₃NO₄Si
Molecular Weight:674.052
Hs Code.:

Synonyms:(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

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Chemical Property of (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

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Technology Process of (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

There total 6 articles about (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-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: 94.0%

: 888323-18-0
(2R,3R,4S,5S)-4-Benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidin-3-ol

: 100-39-0
benzyl bromide

: 888323-23-7
(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

Guidance literature:: With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; for 6h; Heating;
DOI:10.1016/j.tetlet.2006.02.157

Reference yield:

: Methanesulfonic acid (2S,3S,4S,5R)-3-benzyloxy-5-benzyloxymethyl-5-((R)-3,3-dimethyl-oxiranyl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

: 888323-23-7
(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

Guidance literature:: Multi-step reaction with 5 steps

1: 16 h / 90 °C

2: TFA / H₂O / 28 h

3: NaBH₃CN; AcOH / methanol / 48 h

4: 76 percent / imidazole / dimethylformamide / 22 h

5: 94 percent / NaH; n-Bu₄NF / tetrahydrofuran / 6 h / Heating

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; sodium cyanoborohydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.02.157

Reference yield:

: 888323-17-9
(2R,3R,4R,5S)-4-Benzyloxy-2-benzyloxymethyl-1-nonyl-piperidine-3,5-diol

: 888323-23-7
(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / imidazole / dimethylformamide / 22 h

2: 94 percent / NaH; n-Bu₄NF / tetrahydrofuran / 6 h / Heating

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.02.157