[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester

Base Information

Chemical Name:[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester
CAS No.:476330-50-4
Molecular Formula:C₂₅H₂₉NO₁₃
Molecular Weight:551.504
Hs Code.:

Synonyms:[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester

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Chemical Property of [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester

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Technology Process of [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester

There total 10 articles about [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester 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: 56.0%

: 476330-49-1
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-bromoacetic acid 2-cyanoethyl ester

: 476330-50-4
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester

Guidance literature:: With silver nitrate; silver carbonate; In water; acetone; at 20 ℃; for 0.5h; in dark;
DOI:10.1016/j.carres.2005.12.005

Reference yield:

: 476330-48-0
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester

: 476330-50-4
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / NBS; AIBN / CCl₄ / 1 h / Irradiation

2: 56 percent / AgNO₃; Ag₂CO₃ / acetone; H₂O / 0.5 h / 20 °C / in dark

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); silver nitrate; silver carbonate; In tetrachloromethane; water; acetone;
DOI:10.1016/j.carres.2005.12.005

Reference yield:

: 27727-37-3
benzyl p-hydroxyphenylacetate

: 476330-50-4
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-hydroxyacetic acid 2-cyanoethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 67 percent / AgOTf / CH₂Cl₂ / 2 h / cooling

2: 91 percent / H₂; MeOH / Pd/C / ethyl acetate / 1 h / 20 °C

3: 95 percent / DCC; DMAP / CH₂Cl₂ / 10 h / 20 °C

4: 92 percent / NBS / AlBN / CCl₄ / 1 h / Irradiation

5: 55 percent / AgNO₃; Ag₂CO₃ / acetone; H₂O / 0.5 h / 20 °C

With methanol; dmap; N-Bromosuccinimide; hydrogen; silver trifluoromethanesulfonate; silver nitrate; dicyclohexyl-carbodiimide; silver carbonate; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1021/ol0265315