3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

Base Information

Chemical Name:3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose
CAS No.:851050-35-6
Molecular Formula:C₂₈H₅₀O₆Si₂
Molecular Weight:538.872
Hs Code.:

Synonyms:3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

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Chemical Property of 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

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Technology Process of 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

There total 6 articles about 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose 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: 71.0%

: 72261-44-0
1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

: 18162-48-6
tert-butyldimethylsilyl chloride

: 851050-35-6
3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 35 ℃; for 20h;
DOI:10.1016/j.bmc.2005.01.029

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 851050-35-6
3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: sodium periodate / tetrahydrofuran; H₂O / 2 h / 0 °C

2: 30.39 g / NaOH / dioxane; H₂O / 42 h / 20 °C

3: 71 percent / imidazole / dimethylformamide / 20 h / 35 °C

With 1H-imidazole; sodium hydroxide; sodium periodate; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2005.01.029

Reference yield:

: 100-39-0
benzyl bromide

: 851050-35-6
3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 20 °C

2: aq. acetic acid / 22 h

3: sodium periodate / tetrahydrofuran; H₂O / 2 h / 0 °C

4: 30.39 g / NaOH / dioxane; H₂O / 42 h / 20 °C

5: 71 percent / imidazole / dimethylformamide / 20 h / 35 °C

With 1H-imidazole; sodium hydroxide; sodium periodate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2005.01.029