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

Base Information

Chemical Name:[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-bromoacetic acid 2-cyanoethyl ester
CAS No.:476330-49-1
Molecular Formula:C₂₅H₂₈BrNO₁₂
Molecular Weight:614.401
Hs Code.:

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

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

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

There total 9 articles about [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-bromoacetic 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: 92.0%

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

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

Guidance literature:: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 1h; Irradiation;
DOI:10.1021/ol0265315

Reference yield:

: 27727-37-3
benzyl p-hydroxyphenylacetate

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

Guidance literature:: Multi-step reaction with 4 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

With methanol; dmap; N-Bromosuccinimide; hydrogen; silver trifluoromethanesulfonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane; ethyl acetate;
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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With dmap; N-Bromosuccinimide; dicyclohexyl-carbodiimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; dichloromethane;
DOI:10.1021/ol0265315