[(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester

Base Information

• Chemical Name: [(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester
• CAS No.: 880490-79-9
• Molecular Formula: C₂₃H₂₇NO₁₀
• Molecular Weight: 477.468

Synonyms:[(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester

Chemical Property of [(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester

Chemical Property:

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Technology Process of [(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester

There total 2 articles about [(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic 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: 40.0%

(4-hydroxy-phenyl)-acetic acid 2-cyano-ethyl ester (880490-76-6) + 1,2,3,4-tetra-O-acetyl-L-fucopyranose (7404-35-5,17081-04-8,20853-37-6,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,24332-95-4) → [(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester (880490-79-9)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.carres.2005.12.005

Reference yield:

4-hydroxyphenylacetate (156-38-7) → [(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester (880490-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / Na₂SO₄ / H₂SO₄ / acetonitrile / 16 h / Heating

2: 40 percent / BF₃-etherate / acetonitrile / 24 h / 20 °C

With boron trifluoride diethyl etherate; sodium sulfate; sulfuric acid; In acetonitrile;

DOI:10.1016/j.carres.2005.12.005

Reference yield: 83.0%

[(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]acetic acid 2-cyanoethyl ester (880490-79-9) → [(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]bromoacetic acid 2-cyanoethyl ester (880490-84-6)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 1h; Irradiation;

DOI:10.1016/j.carres.2005.12.005

upstream raw materials:

(4-hydroxy-phenyl)-acetic acid 2-cyano-ethyl ester

1,2,3,4-tetra-O-acetyl-L-fucopyranose

4-hydroxyphenylacetate

Downstream raw materials:

[(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]bromoacetic acid 2-cyanoethyl ester

[(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]hydroxyacetic acid 2-cyanoethyl ester

[(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]fluoroacetic acid 2-cyanoethyl ester

N-[(4-tri-O-acetyl-α-L-fucopyranosyloxy)phenyl]fluoroacetyl-N'-biotinylcystamine

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