2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

Base Information

• Chemical Name: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate
• CAS No.: 1219934-69-6
• Molecular Formula: C₂₇H₃₂O₁₁
• Molecular Weight: 532.544
• Mol file: 1219934-69-6.mol

Synonyms:2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

Chemical Property of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

There total 3 articles about 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 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: 90.0%

2-(1-hexyn-1-yl)benzoic acid (120870-47-5) + β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1219934-69-6)

Guidance literature:

β-D-glucose pentaacetate; With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃; for 21h;

2-(1-hexyn-1-yl)benzoic acid; With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In dichloromethane; water; at 20 ℃; for 24h;

DOI:10.1039/c1cc11680k

Reference yield: 71.0%

2-(1-hexyn-1-yl)benzoic acid (120870-47-5) + ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1219934-69-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1219934-68-5)

Guidance literature:

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside; With rhodium (II) octanoate dimer; methyl 2-(4-chlorophenyl)-2-diazoacetate; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve;

2-(1-hexyn-1-yl)benzoic acid; With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 1h; Overall yield = 92 percent; Molecular sieve;

DOI:10.1021/jacs.9b04619

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) + 2-(1-hexyn-1-yl)benzoic acid (120870-47-5) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1219934-69-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1219934-68-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1002/chem.200902548

upstream raw materials:

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

2-(1-hexyn-1-yl)benzoic acid

β-D-glucose pentaacetate

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose

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

n-pent-4-enyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside

n-pent-4-enyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside