triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

Base Information

Chemical Name:triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate
CAS No.:476330-52-6
Molecular Formula:C₂₂H₂₅FO₁₂
Molecular Weight:500.432
Hs Code.:

Synonyms:triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

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Chemical Property of triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

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Technology Process of triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

There total 8 articles about triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate 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: 95.0%

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

: 476330-52-6
triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ol0265315

Reference yield:

: 27727-37-3
benzyl p-hydroxyphenylacetate

: 476330-52-6
triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

Guidance literature:: Multi-step reaction with 7 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

7: 95 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

With methanol; dmap; N-Bromosuccinimide; hydrogen; silver trifluoromethanesulfonate; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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

Reference yield:

: 476330-54-8
[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acetic acid

: 476330-52-6
triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / DCC; DMAP / CH₂Cl₂ / 10 h / 20 °C

2: 92 percent / NBS / AlBN / CCl₄ / 1 h / Irradiation

3: 55 percent / AgNO₃; Ag₂CO₃ / acetone; H₂O / 0.5 h / 20 °C

4: 85 percent / DAST / CH₂Cl₂ / 15 h / 20 °C

5: 95 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; N-Bromosuccinimide; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; 4,4'-diaminostilbene-2,2'-disulfonic acid; silver carbonate; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane; water; acetone;
DOI:10.1021/ol0265315