6-Deoxy-6-iodo-α-D-glucopyranose 1,2,3,4-tetraacetate

Base Information

• Chemical Name: 6-Deoxy-6-iodo-α-D-glucopyranose 1,2,3,4-tetraacetate
• CAS No.: 24871-54-3
• Molecular Formula: C14H19 I O9
• Molecular Weight: 458.1997
• Hs Code.: 2932990090
• Mol file: 24871-54-3.mol

Synonyms:Glucopyranose,6-deoxy-6-iodo-, tetraacetate, a-D- (8CI); a-D-Glucopyranose,6-deoxy-6-iodo-, tetraacetate (9CI); 6-Deoxy-6-iodo-a-D-glucopyranose tetraacetate; NSC 403475

Chemical Property of 6-Deoxy-6-iodo-α-D-glucopyranose 1,2,3,4-tetraacetate

Chemical Property:

• Vapor Pressure: 5.17E-08mmHg at 25°C
• Boiling Point: 442.1°Cat760mmHg
• Flash Point: 221.2°C
• PSA: 114.43000
• Density: 1.62g/cm³
• LogP: 0.50450

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Deoxy-6-iodo-α-D-glucopyranose 1,2,3,4-tetraacetate

There total 11 articles about 6-Deoxy-6-iodo-α-D-glucopyranose 1,2,3,4-tetraacetate 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: 88.0%

acetic anhydride (108-24-7) + methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside (6304-96-7) → acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside (24871-54-3)

Guidance literature:

With sulfuric acid; at 22 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.04.035

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside (24871-54-3)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole; triphenylphosphine; iodine / toluene / 2.5 h / Heating

2: pyridine / 12 h

3: sulphuric acid / 12 h / 20 °C

With pyridine; 1H-imidazole; sulfuric acid; iodine; triphenylphosphine; In toluene;

DOI:10.1021/jo035763u

Reference yield:

Sucrose (57-50-1) → acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside (24871-54-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / iodine, imidazole, triphenylphosphine / dimethylformamide / 1.5 h / 80 °C

2: 36 percent / pyridinium poly(hydrogen fluoride) / 0.33 h / 20 °C

3: conc. H₂SO₄, glacial AcOH / 0 °C

With 1H-imidazole; sulfuric acid; iodine; pyridine hydrogenfluoride; acetic acid; triphenylphosphine; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(94)00239-8

upstream raw materials:

1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose

1,2,3,4-Tetra-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranose

6-iodo-D-6-deoxy-glucose

acetic anhydride

Downstream raw materials:

6-Desoxy-6-iod-2,3,4-tri-O-acetyl-α-D-glucopyranosylbromid

Refernces

• 1、 McDonnell, Ciaran,Cronin, Linda,O'Brien, Julie L.,Murphy, Paul V.. "A General Synthesis of Iminosugars". . p. 3565 - 3568. Retrieved 2007/10/03.