2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid

Base Information

• Chemical Name: 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid
• CAS No.: 83448-12-8
• Molecular Formula: C₂₂H₂₇NO₁₁
• Molecular Weight: 481.456
• Mol file: 83448-12-8.mol

Synonyms:2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid

Chemical Property of 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid

There total 2 articles about 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid 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: 80.0%

(RS)-mandelamide (4410-31-5,24008-62-6,24008-63-7,4358-86-5) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid (83448-12-8)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In 1,2-dichloro-ethane; at 84 ℃; for 0.0833333h;

Reference yield:

(RS)-mandelamide (4410-31-5,24008-62-6,24008-63-7,4358-86-5) + 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,127061-80-7,142831-80-9) → (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)(phenyl)acetamide + 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid (83448-12-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; Overall yield = 65 %; Overall yield = 528 mg; diastereoselective reaction;

DOI:10.1080/07328303.2015.1105249

Reference yield: 84.0%

2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetamid (83448-12-8) → 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetonitril (60981-44-4,60981-47-7,83509-00-6)

Guidance literature:

With pyridine; trifluoroacetic anhydride; for 2h; Ambient temperature;

upstream raw materials:

(RS)-mandelamide

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

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate

Downstream raw materials:

2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenylacetonitril

2-(β-D-Glucopyranosyloxy)-2-phenylacetonitril