1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose
• CAS No.: 136573-67-6
• Molecular Formula: C₂₄H₂₃IO₉
• Molecular Weight: 582.346
• Mol file: 136573-67-6.mol

Synonyms:

Chemical Property of 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose

There total 6 articles about 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose 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:

acetic anhydride (108-24-7) + 1,6-anhydro-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose (136573-61-0) → 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose (136573-67-6) + 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-α-D-glucopyranose (136573-68-7)

Guidance literature:

With sulfuric acid; acetic acid; In dichloromethane; at 0 ℃; for 15h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3) → 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose (136573-67-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 0 - 20 °C

2: 2percent p-toluenesulfonic acid (pTSA) / methanol / 2 h / -5 °C

3: 70 percent / iodonium di-sym-collidine perchlorate (IDCP) / CH₂Cl₂ / Ambient temperature

4: AcOH, concd H₂SO₄ / CH₂Cl₂ / 15 h / 0 °C

With pyridine; iodonium(di-γ-collidine) perchlorate; sulfuric acid; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane;

Reference yield:

benzoyl chloride (98-88-4) → 1,6-di-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose (136573-67-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 0 - 20 °C

2: 2percent p-toluenesulfonic acid (pTSA) / methanol / 2 h / -5 °C

3: 70 percent / iodonium di-sym-collidine perchlorate (IDCP) / CH₂Cl₂ / Ambient temperature

4: AcOH, concd H₂SO₄ / CH₂Cl₂ / 15 h / 0 °C

With pyridine; iodonium(di-γ-collidine) perchlorate; sulfuric acid; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane;

upstream raw materials:

acetic anhydride

1,6-anhydro-3,4-di-O-benzoyl-2-deoxy-2-iodo-β-D-glucopyranose

6-O-tert-butyldimethylsilyl-D-glucal

benzoyl chloride

Refernces