1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Base Information

• Chemical Name: 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• CAS No.: 37812-69-4
• Molecular Formula: C₂₄H₂₆O₁₀
• Molecular Weight: 474.464
• Mol file: 37812-69-4.mol

Synonyms:1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Chemical Property of 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

There total 3 articles about 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-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:

2-naphthyl trimethylsilyl ether (18081-08-8) + 1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside (89825-07-0) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-89-6) + 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (37812-69-4)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 24h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)85681-6

Reference yield:

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + naphthalene-2-boronic acid (32316-92-0) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-89-6) + 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (37812-69-4)

Guidance literature:

naphthalene-2-boronic acid; With pyridine; copper(II) acetate monohydrate; In 1,2-dichloro-ethane; for 0.0833333h; Molecular sieve;

2,3,4,5-tetra-O-acetyl-D-glucopyranose; In 1,2-dichloro-ethane; at 20 ℃; for 24h; Overall yield = 86 percent; Overall yield = 203 mg; Molecular sieve;

DOI:10.1021/acs.joc.9b01218

Reference yield:

Zinc; naphthalen-2-olate + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-89-6) + 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (37812-69-4)

Guidance literature:

With pyridine; acetic anhydride; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, reflux, 4 h, 2.) room temperature, 24 h;

DOI:10.1016/0008-6215(96)00011-0

upstream raw materials:

2-naphthyl trimethylsilyl ether

1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside

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

2,3,4,5-tetra-O-acetyl-D-glucopyranose

Downstream raw materials:

naphthyl-beta-D-glucopyranoside

[2]naphthyl-α-D-glucopyranoside