5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

Base Information

Chemical Name:5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose
CAS No.:1233484-11-1
Molecular Formula:C₃₉H₄₂O₆Si
Molecular Weight:634.844
Hs Code.:

Synonyms:5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

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Chemical Property of 5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

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Technology Process of 5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

There total 18 articles about 5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-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: 96.0%

: 140-10-3
(E)-3-phenylacrylic acid

: 1233484-17-7
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

: 1233484-11-1
5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 50h;
DOI:10.1016/j.tetlet.2010.04.114

Reference yield: 90.0%

: 1233484-15-5
3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1233484-11-1
5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 47h;
DOI:10.1016/j.tetlet.2010.04.114

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 1233484-11-1
5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: periodic acid / ethyl acetate / 20 h / 20 °C

2: N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; toluene / 76 h / 0 - 20 °C / Inert atmosphere

3: 1H-imidazole / dichloromethane / 48 h / 20 °C

4: dmap; dicyclohexyl-carbodiimide / dichloromethane / 50 h / 20 °C

With 1H-imidazole; dmap; N,N,N,N,-tetramethylethylenediamine; periodic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 2: |Grignard Reaction;
DOI:10.1016/j.tet.2015.05.040