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

Base Information

Chemical Name:[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetic acid 2-cyanoethyl ester
CAS No.:476330-51-5
Molecular Formula:C₂₅H₂₈FNO₁₂
Molecular Weight:553.495
Hs Code.:

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

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

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

There total 11 articles about [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetic 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: 86.0%

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

: 476330-51-5
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetic acid 2-cyanoethyl ester

Guidance literature:: With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at 20 ℃; for 15h;
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

: 476330-51-5
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetic acid 2-cyanoethyl ester

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 86 percent / DAST / CH₂Cl₂ / 15 h / 20 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); silver nitrate; 4,4'-diaminostilbene-2,2'-disulfonic acid; silver carbonate; In tetrachloromethane; dichloromethane; water; acetone;
DOI:10.1016/j.carres.2005.12.005

Reference yield:

: 27727-37-3
benzyl p-hydroxyphenylacetate

: 476330-51-5
[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetic acid 2-cyanoethyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 85 percent / DAST / CH₂Cl₂ / 15 h / 20 °C

With methanol; dmap; N-Bromosuccinimide; hydrogen; silver trifluoromethanesulfonate; silver nitrate; dicyclohexyl-carbodiimide; 4,4'-diaminostilbene-2,2'-disulfonic acid; silver carbonate; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1021/ol0265315