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

Base Information

• Chemical Name: [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester
• CAS No.: 476330-48-0
• Molecular Formula: C₂₅H₂₉NO₁₂
• Molecular Weight: 535.505
• Mol file: 476330-48-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-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: 95.0%

3-Hydroxypropionitrile (109-78-4) + [4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acetic acid (476330-54-8) → [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester (476330-48-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 10h;

DOI:10.1021/ol0265315

Reference yield:

benzyl p-hydroxyphenylacetate (27727-37-3) → [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester (476330-48-0)

Guidance literature:

Multi-step reaction with 3 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

With methanol; dmap; hydrogen; silver trifluoromethanesulfonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/ol0265315

Reference yield:

[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid benzyl ester (476330-47-9) → [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester (476330-48-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 95 percent / DCC; DMAP / CH₂Cl₂ / 10 h / 20 °C

With methanol; dmap; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/ol0265315

upstream raw materials:

3-Hydroxypropionitrile

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

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

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

Downstream raw materials:

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

N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

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

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