(2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol

Base Information

• Chemical Name: (2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol
• CAS No.: 80018-68-4
• Molecular Formula: C₂₃H₂₄O₈
• Molecular Weight: 428.439
• Mol file: 80018-68-4.mol

Synonyms:(2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol

Chemical Property of (2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol

There total 3 articles about (2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol 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: 74.0%

acetic anhydride (108-24-7) + (2S,5S)-2,5-anhydro-1,3:4,6-di-O-benzylidene-2-C-hydroxy-5-C-methoxy-D-threo-hexitol (80018-67-3) → (2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol (80018-68-4)

Guidance literature:

In pyridine; at 0 ℃; for 18h;

DOI:10.1016/S0008-6215(00)84693-5

Reference yield:

1,3:4,6-di-O-benzylidene-D-mannitol (28224-73-9) → (2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol (80018-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: rutenium dioxide, potassium periodate, potassium carbonate / acetone; H₂O / 20 h

2: 80 percent

3: 74 percent / pyridine / 18 h / 0 °C

With ruthenium(IV) oxide; potassium metaperiodate; potassium carbonate; In pyridine; water; acetone;

DOI:10.1016/S0008-6215(00)84693-5

Reference yield:

1,3:4,6-di-O-benzylidene-D-threo-2,5-hexodiulose hydrate (80030-25-7,149199-30-4) → (2R,5S)-2-C-acetoxy-2,5-anhydro-1,3:4,6-di-O-benzylidene-5-C-methoxy-D-threo-hexitol (80018-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent

2: 74 percent / pyridine / 18 h / 0 °C

In pyridine;

DOI:10.1016/S0008-6215(00)84693-5

upstream raw materials:

acetic anhydride

(2S,5S)-2,5-anhydro-1,3:4,6-di-O-benzylidene-2-C-hydroxy-5-C-methoxy-D-threo-hexitol

1,3:4,6-di-O-benzylidene-D-mannitol

1,3:4,6-di-O-benzylidene-D-threo-2,5-hexodiulose hydrate