(8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril

Base Information

• Chemical Name: (8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril
• CAS No.: 61045-19-0
• Molecular Formula: C₂₄H₂₇NO₁₂
• Molecular Weight: 521.478
• Mol file: 61045-19-0.mol

Synonyms:(8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril

Chemical Property of (8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril

There total 5 articles about (8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril 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: 82.7%

sodium cyanide (143-33-9,25596-52-5) + meta-hydroxybenzaldehyde (100-83-4) → α-2-(2,3,4,6-Tetra-O-acetyl-D-glucopyranosyloxy)-2-(3-acetoxyphenyl)acetonitril (41547-58-4,61045-19-0,78187-96-9,78187-97-0)

Guidance literature:

With sodium metabisulfite; In diethyl ether; at 0 ℃; for 1h;

Reference yield:

acetic anhydride (108-24-7) + Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-cyano-(3-hydroxy-phenyl)-methoxy]-tetrahydro-pyran-3-yl ester → (8S)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril (41547-58-4) + (8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril (61045-19-0)

Guidance literature:

With ammonium hydroxide; Yield given. Multistep reaction. Yields of byproduct given; 1) methanol, 24 h, room temp.; 2) 10 h, room temp., pyridine;

Reference yield:

sodium cyanide (143-33-9,25596-52-5) + acetic anhydride (108-24-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (8R)-2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2-(3-acetoxyphenyl)acetonitril (61045-19-0)

Guidance literature:

With mercury(II) cyanide; Yield given. Multistep reaction; 1) nitromethane, benzene, room temp., 21 h; 2) pyridine, room temp., 12 h;

upstream raw materials:

sodium cyanide

meta-hydroxybenzaldehyde

acetic anhydride

3-Acetoxybenzaldehydcyanhydrin

Downstream raw materials:

2-(β-D-Glucopyranosyloxy)-2-(3-hydroxyphenyl)acetonitril

2-(β-D-Glucopyranosyloxy)-2-(3-hydroxyphenyl)acetonitril