2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside

Base Information

• Chemical Name: 2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside
• CAS No.: 935877-23-9
• Molecular Formula: C₅₆H₆₆N₂O₂₇
• Molecular Weight: 1199.14
• Mol file: 935877-23-9.mol

Synonyms:2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside

Chemical Property of 2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside

There total 3 articles about 2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside 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: 78.0%

2-(3,5-dibromophenoxy)ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside (935877-22-8) + 4-pyridineboronic acid pinacol ester (181219-01-2) → 2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside (935877-23-9)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 70 ℃; for 48h;

DOI:10.1021/ja0693082

Reference yield:

(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-((2R,3R,4S,5R,6R)-3,4-diacetoxy-6-(acetoxymethyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate (17690-94-7,31873-40-2,31873-41-3,35396-13-5,54192-78-8,61139-07-9,61687-84-1,61687-85-2,69349-75-3,76821-26-6,80446-83-9,113473-58-8,116182-08-2,139894-77-2,141847-33-8,151061-59-5,151061-60-8) → 2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside (935877-23-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 17 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

2: 78 percent / K₂CO₃ / dimethylformamide / 12 h / 70 °C

3: 78 percent / potassium phosphate / tetrakistriphenylphosphine palladium⁽⁰⁾ / dioxane / 48 h / 70 °C

With potassium phosphate; boron trifluoride diethyl etherate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0693082

Reference yield:

2-bromoethyl 2,3,6-tri-O-acetyl-4-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl>-β-D-glucopyranoside (223739-28-4) → 2-[3,5-bis(4-pyridyl)phenoxy]ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside (935877-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / K₂CO₃ / dimethylformamide / 12 h / 70 °C

2: 78 percent / potassium phosphate / tetrakistriphenylphosphine palladium⁽⁰⁾ / dioxane / 48 h / 70 °C

With potassium phosphate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/ja0693082

upstream raw materials:

2-(3,5-dibromophenoxy)ethyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranoside

4-pyridineboronic acid pinacol ester

(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-((2R,3R,4S,5R,6R)-3,4-diacetoxy-6-(acetoxymethyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate

2-bromoethyl 2,3,6-tri-O-acetyl-4-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl>-β-D-glucopyranoside