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

Base Information

Chemical Name:(2R,3R,4S,5S)-4-Benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidin-3-ol
CAS No.:888323-18-0
Molecular Formula:C₃₅H₅₇NO₄Si
Molecular Weight:583.927
Hs Code.:

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

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Chemical Property of (2R,3R,4S,5S)-4-Benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidin-3-ol

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Technology Process of (2R,3R,4S,5S)-4-Benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidin-3-ol

There total 5 articles about (2R,3R,4S,5S)-4-Benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidin-3-ol 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: 76.0%

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

: 18162-48-6
tert-butyldimethylsilyl chloride

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

: (2R,3R,4R,5S)-4-Benzyloxy-2-benzyloxymethyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-nonyl-piperidine

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 22h;
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

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

Guidance literature:: Multi-step reaction with 4 steps

1: 16 h / 90 °C

2: TFA / H₂O / 28 h

3: NaBH₃CN; AcOH / methanol / 48 h

4: 76 percent / imidazole / dimethylformamide / 22 h

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

Reference yield:

: (2R,3S,4S,5S)-4-Benzyloxy-2-benzyloxymethyl-2-hydroxymethyl-5-nonylaminomethyl-tetrahydro-furan-3-ol

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

Guidance literature:: Multi-step reaction with 2 steps

1: NaBH₃CN; AcOH / methanol / 48 h

2: 76 percent / imidazole / dimethylformamide / 22 h

With 1H-imidazole; sodium cyanoborohydride; acetic acid; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.02.157