(2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

Base Information

Chemical Name:(2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol
CAS No.:174222-00-5
Molecular Formula:C₂₇H₄₃N₃O₃Si₂
Molecular Weight:513.828
Hs Code.:

Synonyms:(2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

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Chemical Property of (2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

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Technology Process of (2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

There total 5 articles about (2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol 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: 89.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 174221-96-6
(2R,3S)-5-azido-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

: 174222-00-5
(2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

Guidance literature:: With 1H-imidazole; dmap; In tetrahydrofuran; for 24h; Ambient temperature;
DOI:10.1021/jo951444u

Reference yield:

: 125827-92-1
(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidenepentane-1,2,3,5-tetrol

: 174222-00-5
(2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 9 h / Ambient temperature

2: NaN₃ / dimethylformamide / 12 h / 65 °C

3: 96 percent / aq. HOAc / 24 h / Ambient temperature

4: 89 percent / imidazole, DMAP / tetrahydrofuran / 24 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium azide; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo951444u

Reference yield:

: 160998-95-8
(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

: 174222-00-5
(2R,3S)-5-azido-1-O-(tert-butyldimethylsilyl)-3-O-(tert-butyldiphenylsilyl)pentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 2.) room temperature

2: pyridine / 9 h / Ambient temperature

3: NaN₃ / dimethylformamide / 12 h / 65 °C

4: 96 percent / aq. HOAc / 24 h / Ambient temperature

5: 89 percent / imidazole, DMAP / tetrahydrofuran / 24 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; sodium azide; ozone; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo951444u